Liquid-crystal alkenyltolan derivative, liquid-crystal composition, and liquid-crystal display element

ABSTRACT

A liquid crystalline alkenyltolan derivative expressed by the general formula 
     
       
         C t H 2t−1 —G—(CH 2 ) m —A 1 —B 1 —(A 2 —B 2 ) n —(A 3 —B 3 ) p —A 4 —X 
       
     
     wherein A 1 , A 2 , A 3 , and A 4  independently represent a 1,4-cyclohexylene, 1,4-phenylene in which one or two hydrogen atoms may be replaced by a fluorine atom(s), dioxane-2,5-diyl, or pyrimidine-2,5-diyl group; B 1 , B 2 , and B 3  independently represent a covalent bond, an 1,2-ethylene, 1,2-ethenylene, 1,2-ethynylene, oxymethylene, methylenoxy, carbonyloxy, or 1,4-butylene group provided that at least one of B 1 , B 2 , and B 3  represents an 1,2-ethynylene group; G represents a covalent bond or an oxygen atom; C t H 2t−1  represents an alkenyl group having t carbon atoms; n and p are each 0 or 1; and X represents an alkyl group having 1 to 10 carbon atoms. The derivative provides a liquid-crystal compound and a liquid-crystal composition which have high anisotropy, high elastic constant ratio, excellent comparability with other liquid-crystal compounds, and low viscosity and are chemically and physically stable.

TECHNICAL FIELD

Present invention relates to a tolan derivative, novel liquidcrystalline compounds exhibiting useful physical properties; to liquidcrystal compositions comprising the derivative and exhibiting usefulphysical properties; and to liquid crystal display devices including theliquid crystal composition.

BACKGROUND ART

Liquid crystal display devices utilize optical anisotropy and dielectricanisotropy of liquid crystalline compounds. As display mode of thedevices, twisted nematic (TN) mode, super twisted nematic (STN) mode,dynamic scattering (DS) mode, guest-host (GH) mode, and DAP (Deformationof Aligned Phases) mode have been known. As driving mode for the displaydevices, static driving mode, time shearing addressing mode, activematrix driving mode, and two-frequency addressing mode have been known.

Liquid crystal compositions used for these liquid crystal displaydevices are required to exhibit liquid crystal phase at wide temperaturerange and to be stable against heat, light, moisture, air, electricfield, and electromagnetic radiation. Accordingly, several kind ofliquid crystal compounds are used in combination for display devicematerials. Sometimes, number of the liquid crystal compounds becomesmore than 20 and therefore each of the liquid crystal compounds isrequired to be good in miscibility with other liquid crystal compounds.Particularly, since the display devices have recently come to be used insevere environments, improvement of miscibility at low temperatures hascome to be required. Besides, in keeping with demand for display devicesof higher qualities, improvements of liquid crystal compositions in thespeed for responding to the change of electric field and in thesteepness are required, and thus it has become necessary to controlphysical properties such as dielectric anisotropy and ratio of elasticconstants to most suitable values depending on the display mode and theshape of the devices.

Another characteristic required of effective liquid crystal displaydevices is that the devices have a good display contrast and wideviewing angle. For this purpose, it is necessary to keep the product(Δn·d) of optical anisotropy (Δn) multiplied by cell thickness (d) at aconstant value. One method for increasing the response speed is toreduce the cell thickness (d). Accordingly, in order to achieve thispurpose while maintaining the product (Δn·d) described above at adesired value, liquid crystal compositions having high An are necessaryand in order to produce such liquid crystal compositions, liquidcrystalline compounds having high Δn become necessary.

As compounds having comparatively high Δn, tolan compounds expressed bythe general formula (10) are disclosed in Laid-open Japanese PatentPublication No. Sho 61-5031, alkynyloxytolan compounds expressed by thegeneral formula (11) are disclosed in Laid-open Japanese PatentPublication No. Hei 2-207056, alkynyltolan compounds expressed by thegeneral formula (12) are disclosed in Laid-open Japanese PatentPublication No. Hei 2-180840, allylcyclohexyltolan compounds expressedby the general formula (13) are disclosed in Laid-open Japanese PatentPublication No. Hei 3-58944, and fluorotolan type alkenyl compoundsexpressed by the general formula (14) are disclosed in Laid-openJapanese Patent Publication No. Hei 5-65236, respectively.

wherein Rc represents an alkyl group having 1 to 8 carbon atoms,

Rd represents an alkenyl group having 2 to 14 carbon atoms, and

X represents H or F.

However, the compounds expressed by the general formula (10) are notsufficiently high in Δn and dielectric anisotropy, and the compoundsexpressed by the general formula (11) or (12) have such defects that theviscosity of the compounds is high since they have triple bond at alateral chain and the compounds are poor in miscibility. With respect tothe compounds expressed by the general formula (13), data indicatingtheir liquid crystallinity are not shown. Further, with respect to thecompounds expressed by the general formula (14), whereas a fluorineatom(s) is introduced into a benzene ring, the increase of the value ofΔn is not sufficient.

DISCLOSURE OF THE INVENTION

An object of the present invention is to provide novel liquid crystalcompounds compensating the defects in the prior art, that is, tolanderivatives which are novel liquid crystalline compounds having asufficiently high Δn, high dielectric anisotropy, large ratio of elasticconstants, excellent miscibility with other liquid crystal compounds,and low viscosity, and being chemically and physically stable. Anotherobject of the present invention is to provide liquid crystalcompositions comprising the tolan derivative, and to provide liquidcrystal display devices including the liquid crystal composition.

As a result of the investigation by the present inventors to solve theproblems described above, compounds having a novel structure, andexhibiting improved characteristics compared with known liquidcrystalline compounds have been found to accomplish the presentinvention.

The present invention is summarized as follows:

(1) A liquid crystalline alkenyltolan derivative expressed by thegeneral formula (1)

C_(t)H_(2t−1)—G—(CH₂)_(m)—A₁—B₁—(A₂—B₂)_(n)—(A₃—B₃)_(p)—A₄—X  (1)

 wherein A₁, A₂, A₃, and A₄ independently represent a 1,4-cyclohexylene,1,4-phenylene in which one or two hydrogen atoms may be replaced by afluorine atom(s), dioxane-2,5-diyl, or pyrimidine-2,5-diyl group; B₁,B₂, and B₃ independently represent a covalent bond, an 1,2-ethylene,1,2-ethenylene, 1,2-ethynylene, oxymethylene, methylenoxy, carbonyloxy,or 1,4-butylene group provided that at least one of B₁, B₂, and B₃represents an 1,2-ethynylene group; G represents a covalent bond or anoxygen atom; C_(t)H_(2t−1) represents an alkenyl group having t carbonatoms wherein t is an integer of 2 to 10; m is an integer of 0 to 2; nand p are independently an integer of 0 or 1; X represents an alkylgroup having 1 to 10 carbon atoms, a fluoroalkyl group having 1 to 10carbon atoms, a chlorine atom, a bromine atom, or a cyano group whereinone or more methylene groups or fluoromethylene groups in the alkylgroup or the fluoroalkyl group may be replaced by an oxygen atom(s) oran 1,2-ethenylene group, but adjacent two methylene groups should not besimultaneously replaced by them; provided that when A₄ represents1,4-phenylene group which is not substituted with a fluorine atom(s),there is no case that G represents a covalent bond and t+m=3simultaneously; and each element in the molecule may be its isotope.

(2) The liquid crystalline alkenyltolan derivative recited in paragraph(1) above wherein n and p are 0.

(3) The liquid crystalline alkenyltolan derivative recited in paragraph(1) above wherein n is 1 and p is 0.

(4) The liquid crystalline alkenyltolan derivative recited in paragraph(1) above wherein n and p are 1.

(5) The liquid crystalline alkenyltolan derivative recited in paragraph(2) above wherein X represents a chlorine atom, a bromine atom, a cyanogroup, or a fluoroalkyl group having 1 to 10 carbon atoms in which oneor more fluoromethylene groups may be replaced by an oxygen atom(s) or1,2-ethenylene group(s).

(6) The liquid crystalline alkenyltolan derivative recited in paragraph(2) above wherein X represents an alkyl group having 1 to 10 carbonatoms in which one or more methylene groups may be replaced by an oxygenatom(s) or an 1,2-ethenylene group(s); and A₁ and A₄ independentlyrepresent a 1,4-phenylene group in which one or two hydrogen atoms maybe replaced by a fluorine atom(s)

(7) The liquid crystalline alkenyltolan derivative recited in paragraph(2) above wherein G represents a covalent bond, t+m=4, and a double bondexists at a terminal of the molecule.

(8) The liquid crystalline alkenyltolan derivative recited in paragraph(2) above wherein G represents a covalent bond, t+m=5, and a double bondexists at a second position counting from a terminal of the molecule.

(9) The liquid crystalline alkenyltolan derivative recited in paragraph(3) above wherein X represents a chlorine atom, a bromine atom, a cyanogroup, or a fluoroalkyl group having 1 to 10 carbon atoms in which oneor more fluoromethylene groups may be replaced by an oxygen atom(s) oran 1,2-ethenylene group(s).

(10) The liquid crystalline alkenyltolan derivative recited in paragraph(3) above wherein X represents an alkyl group having 1 to 10 carbonatoms in which one or more methylene groups may be replaced by an oxygenatom(s) or an 1,2-ethenylene group(s).

(11) The liquid crystalline alkenyltolan derivative recited in paragraph(10) wherein G represents a covalent bond, t+m=4, and a double bondexists at a terminal of the molecule.

(12) The liquid crystalline alkenyltolan derivative recited in paragraph(10) wherein G represents a covalent bond, t+m=5, and a double bondexists at a second position counting from a terminal of the molecule.

(13) The liquid crystalline alkenyltolan derivative recited in paragraph(11) wherein B₁ represents a covalent bond and B₂ represents an1,2-ethynylene group.

(14) The liquid crystalline alkenyltolan derivative recited in paragraph(12) wherein B₁ represents a covalent bond and B₂ represents an1,2-ethynylene group.

(15) The liquid crystalline alkenyltolan derivative recited in paragraph(13) wherein A₁ represents an 1,4-cyclohexylene group, and A₂ and/or A₄represents an 1,4-phenylene group in which a hydrogen atom(s) may bereplaced by a fluorine atom(s).

(16) The liquid crystalline alkenyltolan derivative recited in paragraph(15) above wherein A₂ and A₄ represent 1,4-phenylene group in which ahydrogen atom(s) is not replaced by a fluorine atom(s).

(17) The liquid crystalline alkenyltolan derivative recited in paragraph(15) above wherein A₂ represents 1,4-phenylene group in which twohydrogen atoms are replaced by fluorine atoms and A₄ represents1,4-phenylene group in which a hydrogen atom(s) is not replaced by afluorine atom(s).

(18) The liquid crystalline alkenyltolan derivative recited in paragraph(3) above wherein G represents a covalent bond, t+m=4, and a double bondexists at a terminal of the molecule.

(19) The liquid crystalline alkenyltolan derivative recited in paragraph(3) above wherein G represents a covalent bond, t+m=5, and a double bondexists at a second position counting from a terminal of the molecule.

(20) The liquid crystalline alkenyltolan derivative recited in paragraph(4) above wherein X represents a chlorine atom, a bromine atom, a cyanogroup, or a fluoroalkyl group having 1 to 10 carbon atoms in which oneor more fluoromethylene groups may be replaced by an oxygen atom(s) oran 1,2-ethenylene group(s).

(21) The liquid crystalline alkenyltolan derivative recited in paragraph(4) above wherein X represents an alkyl group having 1 to 10 carbonatoms in which one or more methylene groups may be replaced by an oxygenatom(s) or an 1,2-ethenylene group(s).

(22) The liquid crystalline alkenyltolan derivative recited in paragraph(21) above wherein A₂ and/or A₄ represents 1,4-phenylene group in whichone or two hydrogen atoms may be replaced by a fluorine atom(s) and B₃represents 1,2-ethynylene group.

(23) The liquid crystalline alkenyltolan derivative recited in paragraph(21) above wherein A₂ and/or A₃ represents an 1,4-phenylene group inwhich one or two hydrogen atoms may be replaced by an fluorine atom(s)and B₂ represents an 1,2-ethynylene group.

(24) The liquid crystalline alkenyltolan derivative recited in paragraph(23) above wherein one or two hydrogen atoms of A₂ and/or A₃ arereplaced by an fluorine atom(s).

(25) The liquid crystalline alkenyltolan derivative recited in paragraph(4) above wherein G represents a covalent bond, t+m=4, and a double bondexists at a terminal of the molecule.

(26) The liquid crystalline alkenyltolan derivative recited in paragraph(4) above wherein G represents a covalent bond, t+m=5, and a double bondexists at a second position counting from a terminal of the molecule.

(27) The liquid crystalline alkenyltolan derivative recited in paragraph(1) above wherein B₁, B₂, and B₃ independently represent a covalentbond, an 1,2-ethylene, 1,2-ethynylene, oxymethylene, methylenoxy,carbonyloxy, or 1,4-butylene group.

(28) A liquid crystal composition comprising at least two components andcomprising at least one liquid crystalline compound recited in any oneof paragraphs (1) to (27) above.

(29) A liquid crystal composition comprising, as a first component, atleast one liquid crystalline compound recited in any one of paragraphs(1) to (27) above, and comprising, as a second component, at least onecompound selected from the group consisting of the compounds expressedby any one of the general formulas (2), (3), and (4)

 wherein R₁ represents an alkyl group or alkyloxy group having 1 to 10carbon atoms; Y represents a fluorine atom or a chlorine atom; Q₁ and Q₂independently represent a hydrogen atom or a fluorine atom; r is 1 or 2;and Z₁ and Z₂ independently represent a covalent bond or —CH₂CH₂—.

(30) A liquid crystal composition comprising, as a first component, atleast one compound recited in any one of paragraphs (1) to (27) above,and comprising, as a second component, at least one compound selectedfrom the group consisting of the compounds expressed by any one of thegeneral formula s (5), (6), (7), (8), and (9)

 wherein R₂ represents an alkyl group having 1 to 10 carbon atoms or analkenyl group having 2 to 10 carbon atoms, and any methylene group(—CH₂—) in the alkyl or the alkenyl group may be replaced by an oxygenatom (—O—), but adjacent two or more methylene groups are not replacedby an oxygen atom(s) simultaneously; Z₃ represents a covalent bond,—CH₂CH₂—, or —COO—; Q₃ and Q₄ independently represent a hydrogen atom ora fluorine atom; (E) represents an 1,4-cyclohexylene, 1,4-phenylene, ordioxane-2,5-diyl group; s is 0 or 1; R₃ represents an alkyl group having1 to 10 carbon atoms; Q₅ represents a hydrogen atom or a fluorine atom;k is 0 or 1; R₄ represents an alkyl group having 1 to 10 carbon atoms;(G₁) represents an 1,4-cyclohexylene or 1,4-phenylene group; Q₆ and Q₇independently represent a hydrogen atom or a fluorine atom; Z₄represents a covalent bond or —COO—; h is 0 or 1; R₅ and R₆independently represent an alkyl group, alkyloxy group, oralkyloxymethyl group, each having 1 to 10 carbon atoms; (H) representsan 1,4-cyclohexylene, pyrimidine-2,5-diyl, or 1,4-phenylene group; (J)represents an 1,4-cyclohexylene or 1,4-phenylene group; Z₅ represents acovalent bond, —CH₂CH₂—, —C≡C—, or —COO—; R₇ represents an alkyl groupor alkyloxy group, each having 1 to 10 carbon atoms; R₈ represents analkyl group, alkyloxy group, or alkyloxymethyl group, each having 1 to10 carbon atoms; (K) represents an 1,4-cyclohexylene orpyrimidine-2,5-diyl group; (L) and (M) independently represent an1,4-cyclohexylene or 1,4-phenylene group; Z₆ represents a covalent bond,—CH₂CH₂—, or —COO—; Z₇ represents a covalent bond, —C≡C—, or —COO—; andQ₈ represents a hydrogen atom or a fluorine atom.

(31) A liquid crystal display device including a liquid crystalcomposition comprising at least 2 components and comprising at least oneliquid crystalline compound recited in any one of paragraphs (1) to (27)above.

(32) A liquid crystal display device including a liquid crystalcomposition recited in any one of paragraphs (28) to (30) above.

BEST MODE FOR CARRYING OUT THE INVENTION

Among the liquid crystalline compounds of the present inventionexpressed by the general formula (1), a group of compounds expressed bythe general formulas (1-a) to (1-s) are preferable.

wherein G, t, m, and X have the same meaning as described above.

Any of these compounds of the present invention is characterized byhaving high Δn. Also, these compounds are excellent in miscibility withother liquid crystal compounds, are low in viscosity, and are highlystable chemically and physically.

Any of liquid crystalline compounds of the present invention exhibitspreferable physical properties. Particularly, compounds expressed by theformulas (1-n) to (1-s) can be used for liquid crystal compositionshaving high upper limit temperature of liquid crystal phase since theyhave high clearing point, and compounds expressed by the formula (1-a)and (1-b) can be used for liquid crystal compositions having low upperlimit temperature of liquid crystal phase.

When liquid crystal compositions having particularly large positivevalue of dielectric anisotropy are produced to lower driving voltage ofdisplay devices, liquid crystalline compounds having suchcharacteristics (P type compounds) are used. Such purpose can beachieved by introducing a halogen atom or cyano group to X in thegeneral formula (1), or by introducing 1,4-phenylene ring in which ahydrogen atom(s) is replaced by a fluorine atom(s) to A₁, A₂, A₃, and/orA₄. Especially, compounds expressed by the formula (1-d), (1-e), (1-g),or (1-k) are P type compounds having particularly remarkablecharacteristics, and are useful for such purpose.

Compounds having negative or small positive dielectric anisotropy (Ntype compounds) are obtained by introducing an alkyl group having smalldipole moment to X in the general formula (1). Particularly, compoundshaving negative dielectric anisotropy can be obtained by introducing1,4-phenylene in which a hydrogen atom(s) at 2 and/or 3 position isreplaced by a fluorine atom(s), to A₁, A₂, A₃ and/or A₄.

Any compounds expressed by the general formula (1) have high Δn, and thecompounds expressed by the formula (1-h), (1-p), (1-q), (1-r), or (1-s)are very useful since they have extremely high Δn.

Not of all liquid crystalline compounds of the present inventionexpressed by the general formula (1) are necessarily exhibit liquidcrystal phase. However, any liquid crystalline compounds expressed bythe general formula (1) have good miscibility with other liquid crystalcompounds and do not lower or reduce the temperature range of nematicphase of the other liquid crystalline compounds when mixed therewith.Accordingly, the liquid crystalline compounds expressed by the generalformula (1) and having excellent optical characteristics as describedabove become useful components for liquid crystal compositions even whenthe compounds themselves do not exhibit liquid crystal phase. Besides,each of the elements in the compounds may be an isotope since thecharacteristics of liquid crystalline compounds expressed by the generalformula (1) are not affected even when the element is replaced by theisotope.

The liquid crystal compositions of the present invention comprise atleast one liquid crystalline compound expressed by the general formula(1) in the range of 0.1 to 99.9% by weight, and the compositionspreferably comprise a first component comprising at least one compoundexpressed by the general formula (1), and a compound selected from thegroup consisting of the compounds expressed by any one of the generalformulas (2) to (9) depending on the physical properties of liquidcrystal compositions to be obtained.

As compounds which are preferably used for the liquid crystalcompositions of the present invention and are expressed by any one ofthe general formulas (2) to (4), the following compounds (2-1) to (4-41)can be mentioned as examples:

wherein R₁ represents an alkyl group or alkyloxy group having 1 to 10carbon atoms.

Any compound expressed by any one of the general formulas (2) to (4) haspositive dielectric anisotropy and are remarkably excellent in heatstability and chemical stability. When liquid crystal compositions forTFT (AM-LCD) are produced, the compounds are particularly useful sincehigh reliability such as high voltage holding ratio and largeresistivity are required for such compositions. Also, when liquidcrystal compositions for STN display mode or ordinary TN display modeare produced, compounds expressed by one of the general formulas (2) to(4) can be used.

In the liquid crystal compositions of the present invention, thecompounds expressed by any one of the general formulas (2) to (4) areused in an amount in the range of 1 to 99% by weight, preferably 10 to97% by weight, and more desirably 40 to 95% by weight based on the totalamount of liquid crystal composition when liquid crystal compositionsfor TFT are produced.

Liquid crystal compositions of the present invention may furthercomprise compounds expressed by any one of the general formulas (5) to(9).

As compounds which are preferably used for the liquid crystalcompositions of the present invention and are expressed by any one ofthe general formulas (5) to (7), the following compounds (5-1) to (7-13)can be mentioned as examples:

wherein R₂ represents an alkyl group having 1 to 10 carbon atoms or analkenyl group having 2 to 10 carbon atoms, and any methylene group inthe alkyl or alkenyl group may be replaced by an oxygen atom(s), but twoor more methylene groups are not continuously replaced by oxygenatom(s); and R₃ and R₄ independently represent an alkyl group having 1to 10 carbon atoms.

Since any compound expressed by any one of the general formulas (5) to(7) has positive and large value of dielectric anisotropy, the compoundare used particularly for the purpose of lowering threshold voltage ofliquid crystal compositions. The compounds are used also for the purposeof widening nematic range such as raising clearing point, and for thepurpose of adjusting viscosity, adjusting optical anisotropy, orimproving the steepness of threshold characteristics.

As the compounds which are preferably used for the liquid crystalcompositions of the present invention and expressed by the generalformula (8) or (9), the following compounds (8-1) to (9-14) can bementioned as examples:

wherein R₅ and R₆ independently represent an alkyl group, alkyloxygroup, or alkyloxymethyl group, each having 1 to 10 carbon atoms; R₇represents an alkyl group or alkyloxy group, each having 1 to 10 carbonatoms; and R₈ represents an alkyl group, alkyloxy group, oralkyloxymethyl group, each having 1 to 10 carbon atoms.

Any compound expressed by the general formula (8) or (9) has negative,or small and positive dielectric anisotropy. The compounds expressed bythe general formula (9) are used for the purpose of widening nematicrange such as raising clearing point of liquid crystal compositionsand/or for the purpose of adjusting optical anisotropy.

As described above, any compound expressed by any one of the generalformulas (5) to (9) is useful in the production of liquid crystalcompositions for ordinary TN display mode, and particularly for STNdisplay mode.

In the liquid crystal compositions of the present invention, thecompounds expressed by any one of the general formulas (5) to (9) areused in an amount in the range of 1- to 99% by weight, preferably 10 to97% by weight, and more desirably 40 to 95% by weight based on the totalamount of liquid crystal composition when liquid crystal compositionsfor TN display mode or STN display mode are produced. Further, compoundsexpressed by any one of the general formulas (2) to (4) may be usedtogether.

By using the liquid crystal compositions of the present invention forTFT liquid crystal display devices, the steepness of thresholdcharacteristic, or viewing angle can be improved. The response speed ofliquid crystal compositions comprising the compounds are improved, sincethe compounds expressed by the general formula (1) have low viscosity.

Liquid crystal compositions of the present invention can be produced byconventional methods, for example, a method wherein various componentsare dissolved each other at high temperature. Further, the liquidcrystal compositions of the present invention can be improved oroptimized as intended according to their uses by adding a suitablesubstance. Such additive is well known in the art and described indetail in the literature. For instance, a chiral dopant or the like canbe added to induce a helical structure of liquid crystals thereby adjustthe required twisting angle, and to avoid the reverse-twist.

Further, a dichroic dye such as merocyanine type, styryl type, azo type,azomethine type, azoxy type, quinophthalone type, anthraquinone type, ortetrazine type dye can be added to the liquid crystal compositions ofthe present invention in the purpose of using the compositions as onesfor guest-host (GH) mode. The liquid crystal compositions of the presentinvention can be used as NCAP prepared by the microencapsulation of anematic liquid crystal, or as liquid crystal compositions for polymerdispersed liquid crystal display devices (PDLCD) represented by polymernetwork liquid crystal display devices (PNLCD) prepared by formingpolymers of three-dimensional reticulated structure in a liquid crystal.Further, the liquid crystal compositions of the present invention can beused as ones for electrically controlled birefringence (ECB) mode ordynamic scattering (DS) mode.

As nematic liquid crystal compositions comprising the liquid crystallinecompounds of the present invention and produced by the methods describedabove, the following examples of composition can be mentioned:

Abbreviation used when the composition examples are indicated aredefined in the following Table 1.

TABLE 1 Left side terminal group Symbol Bonding group SymbolC_(a)H_(2a+1)— a- —CH₂CH₂— 2 C_(a)H_(2a+1)O— aO- —COO— E CaH2a +10cbH2b— aOb- —C≡C— T CH═CHC_(a)H_(2a)— Va- —CH═CH— VC_(a)H_(2a+1)CH═CHC_(b)H_(2b)— aVb- —CF₂O— CF2OC_(a)H_(2a+1)CH═CHC_(b)H_(2b)CH═CHC_(d)H_(2d)— aVbVd- —OCF₂— OCF2CH₂═CHC_(a)H_(2a)O— VaO- Right side terminal Ring structure Symbol groupSymbol

B —F —F

B(F) —Cl —CL

B(F,F) —CN —C

H —CF₃ —CF3

Py —OCF₃ —OCF3

D —OCF₂H —OCF2H

Ch —C_(w)H_(2w+1) —w —OC_(w)H_(2w+1) -Ow —COOCH₃ -EMe

COMPOSITION EXAMPLE 1

V2-HBTB-2 10.0%  V2-HB(F,F)TB-2 8.0% V2-HB-C 12.0%  1V2-HB-C 11.0% 1V2-BEB(F,F)-C 11.0%  2-BTB-1 8.0% 4-BTB-O2 8.0% 5-BTB-O1 6.0% 3-HH-43.0% 3-HH-EMe 3.0% 3-H2BTB-2 4.0% 3-H2BTB-3 4.0% 3-H2BTB-4 4.0%2-H2BTB-3 4.0% 2-H2BTB-2 4.0%

COMPOSITION EXAMPLE 2

V2-HBTB-2 10.0% 3-HB-C 30.0% 5-HB-C 10.0% 2-BTB-1 10.0% 3-HH-4 10.0%3-HHB-1 10.0% 3-HHB-3 11.0% 3-H2BTB-2  3.0% 3-H2BTB-3  3.0% 3-H2BTB-4 3.0%

COMPOSITION EXAMPLE 3

V2-HBTB-2 6.0% V2-BTB-1 9.0% 3O1-BEB(F)-C 11.0%  V2-HB-C 11.0%  3-HB-O23.0% 2-BTB-O1 5.0% 3-BTB-O1 5.0% 4-BTB-O1 5.0% 4-BTB-O2 5.0% 5-BTB-O15.0% 3-HHB-O1 3.0% 3-H2BTB-2 2.0% 3-H2BTB-3 3.0% 3-H2BTB-4 3.0%3-HB(F)TB-2 4.0% 3-HB(F)TB-3 4.0% 3-HB(F)TB-4 4.0% 2-PyBH-3 4.0%3-PyBH-3 4.0% 3-PyBH-2 4.0%

COMPOSITION EXAMPLE 4

V2-BTB-1 5.0% 2-HB(F)-C 14.0%  3-HB(F)-C 13.0%  5-HB(F)-C 9.0% 2-BB-C8.0% 2-BEB-C 12.0%  3-BEB-C 4.0% 2-HHB(F)-C 9.0% 3-HHB(F)-C 12.0% 2-HHB-C 3.0% 3-HHB-C 3.0% 3-PyBB-F 6.0% 5-PyB-F 2.0%

COMPOSITION EXAMPLE 5

V2-HBTB-1 6.0% 3-DB-C 10.0%  4-DB-C 10.0%  2-BEB-C 12.0%  3-BEB-C 4.0%3-HHEBB-C 3.0% 5-HHEBB-C 3.0% 5-HEB-F 3.0% 3-PyB(F)-F 6.0% 3-HEB-O4 8.9%4-HEB-O2 5.9% 5-HEB-O1 5.9% 3-HEB-O2 5.4% 5-HEB-O2 5.9% 1O-BEB-2 3.0%5-HEB-1 3.0% 4-HEB-4 5.0%

COMPOSITION EXAMPLE 6

V1O-HBTB-1 4.0% V2-DBTB-CL 3.0% 3-HHEB-F 2.0% 3-HBEB-F 2.0% 3-HHB-F 4.0%3-HB-O2 14.0%  3-HB-O4 13.0%  3-PyB-4 3.1% 4-PyB-4 3.1% 6-PyB-4 3.2%3-PyB-5 3.2% 4-PyB-5 3.2% 6-PyB-5 3.2% 6-PyB-O5 6.0% 6-PyB-O6 6.0%6-PyB-O7 6.0% 6-PyB-O8 6.0% 2-HHB-1 4.0% 3-HHB-3 6.0% 3-HHB-O1 5.0%

COMPOSITION EXAMPLE 7

V2-BTB-1 5.0% V2-HB(F,F)TB-2 4.0% V2-HB-C 9.0% 1V2-HB-C 9.0% 3-HB-C14.0%  1O1-HB-C 8.0% 2O1-HB-C 4.0% 2-HHB-C 3.0% 3-HHB-C 5.0% 3-HH-410.0%  1O1-HH-5 8.0% 2-BTB-O1 11.0%  3-HHB-1 6.0% 3-HEBEB-1 2.0%3-HEBEB-F 2.0%

COMPOSITION EXAMPLE 8

V2-HB(F,F)TB-2 10.0%  3-H2HB(F,F)-F 8.0% 5-H2HB(F,F)-F 8.0% 3-HHB(F,F)-F8.0% 4-HHB(F,F)-F 6.0% 3-HH2B(F,F)-F 10.0%  5-HH2B(F,F)-F 8.0%3-HBB(F,F)-F 14.0%  5-HBB(F,F)-F 10.0%  3-HHEB(F,F)-F 6.0% 4-HHEB(F,F)-F3.0% 3-HBEB(F,F)-F 3.0% 3-HHBB(F,F)-F 3.0% 3-HH2BB(F,F)-F 3.0%

COMPOSITION EXAMPLE 9

V2-BTB-1 8.0% V2-HBTB-2 5.0% 7-HB(F)-F 14.0%  2-HHB(F)-F 10.0% 3-HHB(F)-F 10.0%  5-HHB(F)-F 10.0%  2-H2HB(F)-F 6.0% 3-H2HB(F)-F 3.0%5-H2HB(F)-F 6.0% 2-HBB(F)-F 7.0% 3-HBB(F)-F 7.0% 5-HBB(F)-F 14.0% 

COMPOSITION EXAMPLE 10

V2-HBTB-CL 6.0% V2-HBTH-1 3.0% 5-HB-CL 7.0% 7-HB(F,F)-F 10.0% 2-HBB(F)-F 8.0% 3-HBB(F)-F 8.0% 5-HBB(F)-F 16.0%  4-HHB-CL 10.0% 5-HHB-CL 5.0% 3-HBB(F,F)-F 11.0%  5-HBB(F,F)-F 11.0%  3-HB(F)VB-2 5.0%

COMPOSITION EXAMPLE 11

1V2-HBTB-1 5.0% 5-H2B(F)-F 4.0% 2-HHB(F)-F 12.0%  3-HHB(F)-F 12.0% 5-HHB (F)-F 12.0%  2-HBB(F)-F 4.0% 3-HBB(F)-F 4.0% 5-HBB(F)-F 8.0%4-H2BB(F)-F 4.0% 3-HHB(F,F)-F 7.0% 5-HHB(F,F)-F 4.0% 3-HH2B(F,F)-F 9.0%5-HH2B(F,F)-F 6.0% 5-H2BB(F,F)-F 5.0% 3-HBB-F 2.0% 5-HHEBB-F 2.0%

COMPOSITION EXAMPLE 12

V2-HB(F,F)TB-2  5.0% V2-HB(F,F)TB-3  5.0% 7-HB(F,F)-F  4.0%3-H2HB(F,F)-F 12.0% 4-H2HB(F,F)-F 10.0% 3-HHB(F,F)-F 10.0% 4-HHB(F,F)-F 5.0% 3-HH2B(F,F)-F 15.0% 5-H2B(F,F)-F 10.0% 3-HBB(F,F)-F 12.0%5-HBB(F,F)-F 10.0% 1O1-HBBH-3  2.0%

COMPOSITION EXAMPLE 13

V2-HB(F,F)TB-2 6.0% V2-BTB-1 4.0% 6-HB-F 8.0% 7-HB-F 8.0% 5-HB-3 5.0%3-HB-O1 5.0% 3-HHB-OCF3 6.0% 4-HHB-OCF3 5.0% 5-HHB-OCF3 5.0% 3-HHEB-OCF32.0% 3-HH2B-OCF3 3.0% 5-HH2B-OCF3 3.0% 3-HH2B-F 3.0% 5-HH2B-F 3.0%3-HBB(F)-F 6.0% 5-HBB(F)-F 5.0% 3-HH2B(F)-F 7.0% 5-HH2B(F)-F 9.0%3-HB(F,F)B(F)-F 2.0% 3-HB(F)BH-3 3.0% 5-HB(F)BH-3 2.0%

COMPOSITION EXAMPLE 14

V2-HBTB-CL 5.0% V2-DBTB-CL 5.0% 5-HB-F 7.0% 3-HH-O1 7.0% 3-HH-O3 6.0%3-HHB-OCHF2 3.0% 5-HHB-OCHF2 4.0% 3-HHB(F,F)-OCHF2 8.0% 5-HHB(F,F)-OCHF28.0% 2-HHB-OCF3 6.0% 3-HHB-OCF3 7.0% 4-HHB-OCF3 6.0% 5-HHB-OCF3 6.0%3-HH2B(F)-F 7.0% 5-HH2B(F)-F 9.0% 3-HHEB(F)-F 6.0%

COMPOSITION EXAMPLE 15

V2-HBTB-2 5.0% V2-HBTB-1 5.0% V-HB-C 10.0%  1V-HB-C 5.0% 5-BB-C 5.0%2-HB(F)-C 5.0% 4-BB-3 3.0% 3-H2B-O2 5.0% 5-H2B-O2 5.0% 3-BEB-C 5.0%5-HEB-O1 8.0% 5-HEB-O3 8.0% 5-BBB-C 5.0% 4-BPyB-C 4.0% 4-BPyB-5 4.0%5-HB2B-4 5.0% 5-HBB2B-3 3.0% 1V-HH-1O1 5.0% 1V2-HBB-3 5.0%

COMPOSITION EXAMPLE 16

V2-BTB-1 8.0% V1O-HBTB-1 8.0% 4-HEB(F)-F 8.0% 5-HEB(F)-F 8.0% 2-BEB(F)-C5.0% 3-BEB(F)-C 5.0% 5-BEB(F)-C 8.0% 1O3-HB(F)-C 6.0% 3-HHEB(F)-F 5.0%5-HHEB(F)-F 5.0% 2-HBEB(F)-C 5.0% 3-HBEB(F)-C 6.0% 5-HBEB(F)-C 5.0%3-HBTB-2 10.0%  V2-HH-3 4.0% V2-HHB-1 4.0%

As described below, the compounds of the present invention expressed bythe general formula (1) can be produced by known general methods oforganic synthesis.

[Case wherein bonding group B₁, B₂, or B₃ represents 1,2-ethynylenegroup, and the ring A₁, A₂, A₃, or A₄ at one side or both sides of thebonding group represents 1,4-phenylene in which a hydrogen atom(s) maybe replaced by a fluorine atom(s), or pyrimidine-2,5-diyl group, in thegeneral formula (1)].

Compounds expressed by the general formula (1) can readily besynthesized by coupling an acetylene derivative expressed by the formula(10) and a halide expressed by the formula (11) in a solvent in thepresence of a catalyst of transition metal complex and a promotor addedwhen necessary, according to, for example, a method described inTetrahedron Lett., vol. 22, p 305 (1981).

wherein G, A₁, A₂, A₃, A₄, B₁, B₂, B₃, X, t, m, n, and p have the samemeaning as described above; q, r, s, b, and u are an integer of 0 or 1;q+b=n; r+u=p, s is 0 when n and p are 0; and Y represents a halogen atomprovided that when X represents a halogen atom, then Y represents ahalogen atom having higher reactivity than X.

As the complex catalyst described above, for example, a zero valent ordivalent palladium complex such as dichlorobistriphenylphosphinepalladium, tetrakistriphenylphosphine palladium, palladium acetate, andkahrasch complex can be mentioned. Whereas the amount of the complexcatalyst to be used depends on the reactivity of substrates and is notconstant, it is suitably in the range of 0.1 to 20% by mol in general,and preferably in the range of 0.5 to 5% by mol, particularly sinceconversion time is short and besides, side reactions hardly occur.

As the promotor, a copper salt such as copper iodide and copper bromideis preferable to increase the yield. As the solvent, while diethylamineis most suitable in general, a polar solvent such as triethylamine,pyridine, morpholine, and dimethyl formamide or a mixed solvent of oneof these solvents with another suitable solvent can also be used.

While reaction temperature is suitably in the range of −40° C. toboiling point of the solvent employed, it is preferably a temperaturebetween 0° C. and the boiling point of the solvent in particular sincethe catalyst activity is satisfactorily maintained and the conversion ishigh. Further, the reaction described above is preferably carried out inan inert gas since the active site of the catalyst is unstable againstair and moisture.

When a compound of the formula (1) of the present invention is isolatedafter finishing of the reaction, it is particularly preferable toconduct, after ordinary treatments, purification such as distillation,recrystallization, or column chromatography to separate the catalystremaining in the reaction mixture.

[Case wherein bonding group B₁, B₂, or B₃ represents a 1,2-ethynylenegroup, and simultaneously the ring A₁, A₂, A₃, or A₄ at both sides ofthe bonding group represents 1,4-cyclohexylene group or dioxane-2,5-diylgroup, in the general formula (1)].

For example, the halogenated vinyl derivative expressed by the formula(14) can readily be synthesized by the known reaction of a phosphoniumsalt expressed by the formula (12) which can readily be preparedaccording to a method described in Organic Reactions, vol. 14, p 270(1965), with an aldehyde expressed by the formula (13) which can readilybe prepared according to a method described in Shin-Jikken Kagaku Kouza(Course of New Chemical Experiment), vol. 14, p 633 (1977), in asuitable solvent in the presence of a base such as potassium-t-butoxide.Objecvtive compounds of the formula (1) can readily be produced bydehydrohalogenation of a compound of the formula (14) in a suitablesolvent in the presence of a base such as potassium-t-butoxide or sodiumamide according to a method described in Shin-Jikken Kagaku Kouza, vol.14, p 253 (1977).

wherein G, A₁, A₂, A₃, A₄, B₁, B₂, B₃, X, t, m, n, and p have the samemeaning as described above; q, r, s, b, and u are an integer of 0 or 1;q+b=n; r+u=p, s is 0 when n and p are 0; and Y represents a halogenatom.

After the reaction, the compound of the formula (1) can be isolated withordinary treatments and purification such as distillation,recrystallization, or column chromatography.

Precursors (16), (18), and (22) of the formula (10) or (12) which arestarting materials for compounds expressed by general formula (1) aresynthesized by the following method:

[Case wherein G represents a covalent bond and a double bond exists at aterminal of an alkenyl group (C_(t)H_(2t−1)) in the general formula(1)].

For example, alkenyl compounds expressed by the formula (16) can readilybe synthesized by the reaction of an aldehyde derivative expressed bythe formula (15) which can readily be prepared according to a methoddescribed in Japanese Patent Publication No. Hei 4-30382 or JapanesePatent Application No. Hei 7-180745 with methyltriphenylphosphoniumbromide in a suitable solvent in the presence of a base such aspotassium-t-butoxide.

wherein A₁, A₂, A₃, B₁, B₂, m, s, b, and u have the same meaning asdescribed above; v is an integer of 1 to 8; and t=v+2 wherein t has thesame meaning as described above.

[Case wherein G represents a covalent bond and a double bond does notexist at a terminal of an alkenyl group (C_(t)H_(2t−1)) in the generalformula (1)].

Alkenyl compounds expressed by the formula (18) can readily besynthesized by the reaction of a compound expressed by the formula (15)with diiodide expressed by the formula (17) in the presence of chrome(II) dichloride according to, for example, a method described in J. Am.Chem. Soc. vol. 109, p 951 (1987).

wherein A₁, A₂, A₃, B₁, B₂, m, s, b, and u have the same meaning asdescribed above; v and w are an integer; and t=v+w+2 wherein t has thesame meaning as described above.

[Case wherein G represents oxygen atom in the general formula (1)].

Alcohol derivatives expressed by the formula (20) can readily besynthesized by the reduction of a compound expressed by the formula (19)which can readily be prepared, for example, by a method described inJapanese Patent Publication No. Hei 4-30382 or Japanese PatentApplication No. Hei 7-180745 with a reducing agent such as sodiumborohydride according to, for example, a method described in J. Am.Chem. Soc., vol. 71, p 122 (1949) or ibid. vol. 74, p 3630 (1952). Then,compounds expressed by the formula (22) can readily be synthesized byreacting a compound of the formula (20) with an alkenyl halide expressedby the formula (21) in the presence of a base such as sodium hydrideaccording to a method described in Shin-Jikken Kagaku Kouza vol. 19, p176 (1957).

wherein A₁, A₂, A₃, B₁, B₂, t, m, s, b, and u have the same meaning asdescribed above; and Y represents a halogen atom.

Compounds of the formula (16), (18), or (22) thus synthesized canreadily be converted into acetylene derivatives expressed by the formula(10) according to, for example, a method described in J. Am. Chem. Soc.,vol. 84, p 1745 (1962) and Tetrahedron Lett., vol. 36, p 3769 (1972), orinto phosphonium salts expressed by the formula (12) according to amethod described in Organic Reactions, vol. 5, p 1 (1949) and ibid.,vol. 14, p 270 (1965), after converting their cyano group into aldehydegroup by treating with a reducing agent such as diisobutyl aluminumhydride according to, for example, a method described in J. Org. Chem.,vol. 24, p 627 (1959).

Now, the methods for producing the compounds of the present inventionand use examples of the compounds will be described in more detail withreference to Examples. In each of the Examples, C indicates-crystal, Nnematic phase, S smectic phase, and I isotropic liquid; and unit ofevery phase transition temperature is ° C.

EXAMPLE 1

Synthesis of 4-(trans-4-(3-butenyl)cyclohexyl)-4′-ethyltolan (Compoundexpressed by the general formula (1) wherein R represents vinyl group; Grepresents a covalent bond; m is 2; n is 1; p is 0; A₁ represents1,4-cyclohexylene group; A₂ and A₄ represent 1,4-phenylene group; B₁represents a covalent bond; B₂ represents 1,2-ethynylene group; and Xrepresents ethyl group. Compound No. 49)

Degasified diethyl amine was added to a mixture ofdichlorobistriphenylphosphine palladium (0.19 mmol) and copper iodide(0.03 mmol), and stirred under argon gas at room temperature for 15 min.To the mixture was added 4-ethyliodobenzene, and they were stirred atroom temperature for further 30 min. To this reaction mixture was added1-ethynyl-4-(trans-4-(3-butenyl)cyclohexyl)benzene, and they werestirred at room temperature one night. After finishing of the reaction,the solvent was distilled off, and the product was purified by columnchromatography (silica gel/heptane) and then recrystallized from heptaneto obtain colorless crystals (yield 89%). Various kind of spectral dataof this compound well supported its structure.

Phase transition point C•58.9•S•115.1•N•175•I

EXAMPLE 2

According to the method of Example 1,4-(trans-4-(3-butenyl)cyclohexyl)-2,6-difluoro-4′-ethyltolan (CompoundNo. 56) was synthesized by using1-ethynyl-4-(trans-4-(3-butenyl)cyclohexyl)-2,6-difluorobenzene in placeof 1-ethynyl-4-(trans-4-(3-butenyl)cyclohexyl)benzene.

Phase transition point C•75.1•N•174.6•I

EXAMPLE 3

According to the method of Example 1,4-(trans-4-(3-E-pentenyl)cyclohexyl)-4′-ethyltolan (Compound No. 50) wassynthesized by using1-ethynyl-4-(trans-4-(3-E-pentenyl)cyclohexyl)benzene in place of1-ethynyl-4-(trans-4-(3-butenyl)cyclohexyl)benzene.

EXAMPLE 4

According to the method of Example 1,4-(trans-4-(2-propenyloxymethyl)cyclohexyl)-4′-ethyltolan (Compound No.63) was synthesized by using1-ethynyl-4-(trans-4-(propenyloxymethyl)cyclohexyl)benzene in place of1-ethynyl-4-(trans-4-(3-butenyl)cyclohexyl)benzene.

EXAMPLE 5

According to the method of Example 1,4-(trans-4-(3-butenyl)cyclohexyl)-4′-ethoxytolan (Compound No. 64) wassynthesized by using 4-ethoxyiodobenzene in place of 4-ethyliodobenzene.

EXAMPLE 6

According to the method of Example 1,4-(trans-4-(3-butenyl)cycloheyxl)-4′-cyanotolan (Compound No. 70) wassynthesized by using 4-cyanoiodobenzene in place of 4-ethyliodobenzene.

EXAMPLE 7

According to the method of Example 1,4-(trans-4-(3-butenyl)cyclohexyl)-4′-chlorotolan (Compound No. 75) wassynthesized by using 4-chloroiodobenzene in place of 4-ethyliodobenzene.

EXAMPLE 8

According to the method of Example 1,4-(trans-4-(3-butenyl)cyclohexyl)-4′-trifluoromethyltolan (Compound No.84) was synthesized by using 4-trifluoromethyliodobenzene in place of4-ethyliodobenzene.

According to Examples 1 to 8 described above, the following compoundsare synthesized:

Compound No. 1

4-(3-butenyl)-4′-methyltolan

Compound No. 2

4-(3-E-pentenyl)-4′-methyltolan

Compound No. 3

4-(2-propenyloxymethyl)-4′-methyltolan

Compound No. 4

4-(3-butenyl)-4′-propyltolan

Compound No. 5

4-(3-E-pentenyl)-4′-propyltolan

Compound No. 6

4-(3-butenyl)-4′-butyltolan

Compound No. 7

4-(3-butenyl)-4′-pentyltolan C•28.6•N•37.2•I

Compound No. 8

4-(3-butenyl)-2,6-difluoro-4′-methyltolan

Compound No. 9

4-(3-E-pentenyl)-2,6-difluoro-4′-methyltolan

Compound No. 10

4-(3-butenyl)-2,6-difluoro-4′-propyltolan

Compound No. 11

4-(3-E-pentenyl)-2,6-difluoro-4′-propyltolan

Compound No. 12

4-(3-butenyl)-4′-ethoxytolan

Compound No. 12-1

4-(3-butenyl)-4′-heptoxytolan C•51.0•N•64.0•I

Compound No. 13

4-(3-E-pentenyl)-4′-ethoxytolan

Compound No. 14

4-(3-butenyl)-4′-cyanotolan

Compound No. 15

4-(3-E-pentenyl)-4′-cyanotolan

Compound No. 16

4-(3-butenyl)-3′-fluoro-4′-cyanotolan

Compound No. 17

4-(3-E-pentenyl)-3′-fluoro-4′-cyanotolan

Compound No. 18

4-(3-butenyl)-4′-chlorotolan

Compound No. 19

4-(3-E-pentenyl)-4′-chlorotolan

Compound No. 20

4-(3-butenyl)-3′-fluoro-4′-chlorotolan

Compound No. 21

4-(3-E-pentenyl)-3′-fluoro-4′-chlorotolan

Compound No. 22

4-(3-butenyl)-4′-bromotolan

Compound No. 23

4-(3-E-pentenyl)-4′-bromotolan

Compound No. 24

4-(3-butenyl)-4′-trifluoromethyltolan

Compound No. 25

4-(3-E-pentenyl)-4′-trifluoromethyltolan

Compound No. 26

4-(3-butenyl)-3′-fluoro-4′-trifluoromethyltolan

Compound No. 27

4-(3-E-pentenyl)-3′-fluoro-4′-trifluoromethyltolan

Compound No. 28

4-(3-butenyl)-4′-trifluoromethoxytolan

Compound No. 29

4-(3-E-pentenyl)-4′-trifluoromethoxytolan

Compound No. 30

4-(3-butenyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 31

4-(3-E-pentenyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 32

1-(trans-4-(3-butenyl)cyclohexyl)ethynyl-4-ethylbenzene

Compound No. 33

1-(trans-4-(3-E-pentenyl)cyclohexyl)ethynyl-4-ethylbenzene

Compound No. 34

1-(trans-4-(3-butenyl)cyclohexyl)ethynyl-4-propylbenzene

Compound No. 35

1-(trans-4-(3-E-pentenyl)cyclohexyl)ethynyl-4-propylbenzene

Compound No. 36

1-(trans-4-(3-butenyl)cyclohexyl)ethynyl-4-ethoxybenzene

Compound No. 37

1-(trans-4-(3-E-pentenyl)cyclohexyl)ethynyl-4-ethoxybenzene

Compound No. 38

1-(trans-4-(3-butenyl)cyclohexyl)ethynyl-4-cyanobenzene

Compound No. 39

1-(trans-4-(3-E-pentenyl)cyclohexyl)ethynyl-4-cyanobenzene

Compound No. 40

1-(trans-4-(3-butenyl)cyclohexyl)ethynyl-4-chlorobenzene

Compound No. 41

1-(trans-4-(3-E-pentenyl)cyclohexyl)ethynyl-4-chlorobenzene

Compound No. 42

1-(trans-4-(3-butenyl)cyclohexyl)ethynyl-4-trifluoromethylbenzene

Compound No. 43

1-(trans-4-(3-E-pentenyl)cyclohexyl)ethynyl-4-trifluoromethylbenzene

Compound No. 44

1-(trans-4-(3-butenyl)cyclohexyl)ethynyl-4-trifluoromethoxybenzene

Compound No. 45

1-(trans-4-(3-E-pentenyl)cyclohexyl)ethynyl-4-trifluoromethoxybenzene

Compound No. 46

1-(trans-4-(3-butenyl)cyclohexyl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxybenzene

Compound No. 47

1-(trans-4-(3-E-pentenyl)cyclohexyl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxybenzene

Compound No. 48

4-(trans-4-(3-butenyl)cyclohexyl)-4′-methyltolan

Compound No. 49

4-(trans-4-(3-butenyl)cyclohexyl)-4′-ethyltolan

Compound No. 50

4-(trans-4-(3-E-pentenyl)cyclohexyl)-4′-ethyltolan

Compound No. 51

4-(trans-4-(3-butenyl)cyclohexyl)-4′-propyltolan

Compound No. 52

4-(trans-4-(3-E-pentenyl)cyclohexyl)-4′-propyltolan

Compound No. 53

4-(trans-4-(3-butenyl)cyclohexyl)-4′-butyltolan

Compound No. 54

4-(trans-4-(3-butenyl)cyclohexyl)-4′-pentyltolan

Compound No. 55

4-(trans-4-(3-butenyl)cyclohexyl)-4′-(3-butenyl)tolan

Compound No. 56

4-(trans-4-(3-butenyl)cyclohexyl)-2,6-difluoro-4′-ethyltolan

Compound No. 57

4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,6-difluoro-4′-ethyltolan

Compound No. 58

4-(trans-4-(3-butenyl)cyclohexyl)-2,6-difluoro-4′-propyltolan

Compound No. 59

4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,6-difluoro-4′-propyltolan

Compound No. 60

4-(trans-4-(2-propenyl)cyclohexyl)-4′-ethyltolan

Compound No. 61

4-(trans-4-(7-octenyl)cyclohexyl)-4′-ethyltolan

Compound No. 62

4-(trans-4-(7-E-nonenyl)cyclohexyl)-4′-ethyltolan

Compound No. 63

4-(trans-4-(2-propenyloxymethyl)cyclohexyl)-4′-ethyltolan

Compound No. 64

4-(trans-4-(3-butenyl)cyclohexyl)-4′-ethoxytolan

Compound No. 65

4-(trans-4-(3-E-pentenyl)cyclohexyl)-4′-ethoxytolan

Compound No. 66

4-(trans-4-(3-butenyl)cyclohexyl)-4′-propoxytolan

Compound No. 67

4-(trans-4-(3-E-pentenyl)cyclohexyl)-4′-propoxytolan

Compound No. 68

4-(trans-4-(3-butenyl)cyclohexyl)-2,6-difluoro-4′-ethoxytolan

Compound No. 69

4-(trans-4-(3-E-pentenyl)cycloheyxl)-2,6-difluoro-4′-ethoxytolan

Compound No. 70

4-(trans-4-(3-butenyl)cyclohexyl)-4′-cyanotolan

Compound No. 71

4-(trans-4-(3-E-pentenyl)cyclohexyl)-4′-cyanotolan

Compound No. 72

4-(trans-4-(3-butenyl)cyclohexyl)-2,6-difluoro-4′-cyanotolan

Compound No. 73

4-(trans-4-(3-butenyl)cyclohexyl)-3′-fluoro-4′-cyanotolan

Compound No. 74

4-(trans-4-(3-E-pentenyl)cyclohexyl)-3′-fluoro-4′-cyanotolan

Compound No. 75

4-(trans-4-(3-butenyl)cyclohexyl)-4′-chlorotolan

Compound No. 76

4-(trans-4-(3-E-pentenyl)cyclohexyl)-4′-chlorotolan

Compound No. 77

4-(trans-4-(3-butenyl)cyclohexyl)-2,6-difluoro-4′-chlorotolan

Compound No. 78

4-(trans-4-(3-butenyl)cyclohexyl)-3′-fluoro-4′-chlorotolan

Compound No. 79

4-(trans-4-(3-E-pentenyl)cyclohexyl)-3′-fluoro-4′-chlorotolan

Compound No. 80

4-(trans-4-(3-butenyl)cyclohexyl)-4′-bromotolan

Compound No. 81

4-(trans-4-(3-E-pentenyl)cyclohexyl)-4′-bromotolan

Compound No. 82

4-(trans-4-(3-butenyl)cyclohexyl)-3′-fluoro-4′-bromotolan

Compound No. 83

4-(trans-4-(3-pentenyl)cyclohexyl)-3′-fluoro-4′-bromotolan

Compound No. 84

4-(trans-4-(3-butenyl)cyclohexyl)-4′-trifluoromethyltolan

Compound No. 85

4-(trans-4-(3-E-pentenyl)cyclohexyl)-4′-trifluoromethyltolan

Compound No. 86

4-(trans-4-(3-butenyl)cyclohexyl)-3′-fluoro-4′-trifluoromethyltolan

Compound No. 87

4-(trans-4-(3-E-pentenyl)cyclohexyl)-3′-fluoro-4′-trifluoromethyltolan

Compound No. 88

4-(trans-4-(3-butenyl)cyclohexyl)-4′-trifluoromethoxytolan

Compound No. 89

4-(trans-4-(3-E-pentenyl)cyclohexyl)-4′-trifluoromethoxytolan

Compound No. 90

4-(trans-4-(3-butenyl)cyclohexyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 91

4-(trans-4-(3-E-pentenyl)cyclohexyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 92

1-(trans-4-(trans-4-(3-butenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-ethylbenzene

Compound No. 93

1-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-ethylbenzene

Compound No. 94

1-(trans-4-(trans-4-(3-butenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-ethoxybenzene

Compound No. 95

1-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-ethoxybenzene

Compound No. 96

1-(trans-4-(trans-4-(3-butenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-cyanobenzene

Compound No. 97

1-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-cyanobenzene

Compound No. 98

1-(trans-4-(trans-4(3-butenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-chlorobenzene

Compound No. 99

1-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-chlorobenzene

Compound No. 100

1-(trans-4-(trans-4-(3-butenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-trifluoromethylbenzene

Compound No. 101

1-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-trifluoromethylbenzene

Compound No. 102

1-(trans-4-(trans-4-(3-butenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-trifluoromethoxybenzene

Compound No. 103

1-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-trifluoromethoxybenzene

Compound No. 104

1-(trans-4-(trans-4-(3-butenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxybenzene

Compound No. 105

1-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-dioxane-1-yl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxybenzene

Compound No. 106

1-(4-(trans-4-(3-butenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-ethylbenzene

Compound No. 107

1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-ethylbenzene

Compound No. 108

1-(4-(trans-4-(3-butenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-ethoxybenzene

Compound No. 109

1-(4-(trans-4-(3-E-pentenyl)cylohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-ethoxybenzene

Compound No. 110

1-(4-(trans-4-(3-butenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-cyanobenzene

Compound No. 111

1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-cyanobenzene

Compound No. 112

1-(4-(trans-4-(3-butenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-chlorobenzene

Compound No. 113

1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-chlorobenzene

Compound No. 114

1-(4-(trans-4-(3-butenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-trifluoromethylbenzene

Compound No. 115

1-(4-(ttans-4-(3-E-pentenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-trifluoromethylbenzene

Compound No. 116

1-(4-(trans-4-(3-butenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-trifluroromethylbenzene

Compound No. 117

1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-trifluoromethoxybenzene

Compound No. 118

1-(4-(trans-4-(3-butenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxybenzene

Compound No. 119

1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)-2,5-pyrimidine-1-yl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxybenzene

Compound No. 120

4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)-4′-methyltolan

Compound No. 121

4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)-4′-methyltolan

Compound No. 122

4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)-4′-propyltolan

Compound No. 123

4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)-4′-propyltolan

Compound No. 124

4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)-2,6-difluoro-4′-methyltolan

Compound No. 125

4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)-2,6-difluoro-4′-methyltolan

Compound No. 126

4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)-4′-ethoxytolan

Compound No. 127

4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)-4′-ethoxytolan

Compound No. 128

4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)-4′-cyanotolan

Compound No. 129

4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)-4′-cyanotolan

Compound No. 130

4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)-3′-fluoro-4′-cyanotlan

Compound No. 131

4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)-3′-fluoro-4′-cyanotolan

Compound No. 132

4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)-4′-chlorotolan

Compound No. 133

4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)-4′-chlorotolan

Compound No. 134

4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)-4′-trifluoromethyltolan

Compound No. 135

4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)-4′-trifluoromethyltolan

Compound No. 136

4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)-4′-trifluoromethoxytolan

Compound No. 137

4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)-4′-trifluoromethoxytolan

Compound No. 138

4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 139

4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 140

4-(trans-4-(3-butenyl)cyclohexyl)carbonyloxy-4′-methyltolan

Compound No. 141

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-4′-methyltolan

Compound No. 142

4-(trans-4-(3-butenyl)cyclohexyl)carbonyloxy-4′-propyltolan

Compound No. 143

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-4′-propyltolan

Compound No. 144

4-(trans-4-(3-butenyl)cyclohexyl)carbonyloxy-2,6-difluoro-4′-methyltolan

Compound No. 145

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-2,6-difluoro-4′-methyltolan

Compound No. 146

4-(trans-4-(3-butenyl)cyclohexyl)carbonyloxy-2,6-difluoro-4′-propyltolan

Compound No. 147

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-2,6-difluoro-4′-propyltolan

Compound No. 148

4-(trans-4-(3-butenyl)cyclohexyl)carbonyloxy-4′-ethoxytolan

Compound No. 149

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-4′-ethoxytolan

Compound No. 150

4-(trans-4-(3-butenyl)cyclohexyl)carbonyloxy-4′-cyanotolan

Compound No. 151

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-4′-cyanotolan

Compound No. 152

4-(trans-4-(3-butenyl)cylohexyl)carbonyloxy-3′-fluoro-4′-cyanotolan

Compound No. 153

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-3′-fluoro-4′-cyanotolan

Compound No. 154

4-(trans-4-(3-butenyl)cyclohexyl)carbonyloxy-4′-chlorotolan

Compound No. 155

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-4′-chlorotolan

Compound No. 156

4-(trans-4-(3-butenyl)cyclohexyl)carbonyloxy-3′-fluoro-4′-chlorotolan

Compound No. 157

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-3′-fluoro-4′-chlorotolan

Compound No. 158

4-(trans-4-(3-butenyl)cyclohexyl)carbonyloxy-4′-trifluoromethyltolan

Compound No. 159

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-4′-trifluoromethyltolan

Compound No. 160

4-(trans-4-(3-butenyl)cyclohexyl)carbonyloxy-4′-trifluoromethoxytolan

Compound No. 161

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-4′-trifluoromethoxytolan

Compound No. 162

4-(trans-4-(3-butenyl)cyclohexyl)carbonyloxy-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 163

4-(trans-4-(3-E-pentenyl)cyclohexyl)carbonyloxy-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 164

4-(4-(3-butenyl)phenyl)-4′-methyltolan

Compound No. 165

4-(4-(3-E-pentenyl)phenyl)-4′-methyltolan

Compound No. 166

4-(4-(2-propenyloxy)phenyl)-4′-methyltolan

Compound No. 167

4-(4-(3-butenyl)phenyl)-4′-propyltolan

Compound No. 168 4-(4-(3-E-pentenyl)phenyl)-4′-propyltolan

Compound No. 169

4-(4-(3-butenyl)phenyl)-2,6-difluoro-4′-methyltolan

Compound No. 170

4-(4-(3-E-pentenyl)phenyl)-2,6-difluoro-4′-methyltolan

Compound No. 171

4-(4-(3-butenyl)phenyl)-2,6-difluoro-4′-propyltolan

Compound No. 172

4-(4-(3-E-pentenyl)phenyl)-2,6-difluoro-4′-propyltolan

Compound No. 173

4-(4-(3-butenyl)phenyl)-4′-ethoxytolan

Compound No. 174

4-(4-(3-E-pentenyl)phenyl)-4′-ethoxytolan

Compound No. 175

4-(4-(3-butenyl)phenyl)-4′-cyanotolan

Compound No. 176

4-(4-(3-E-pentenyl)phenyl)-4′-cyanotolan

Compound No. 177

4-(4-(3-butenyl)phenyl)-3′-fluoro-4′-cyanotolan

Compound No. 178

4-(4-(3-E-pentenyl)phenyl)-3′-fluoro-4′-cyanotolan

Compound No. 179

4-(4-(3-butenyl)phenyl)-4′-chlorotolan

Compound No. 180

4-(4-(3-E-pentenyl)phenyl)-4′-chlorotolan

Compound No. 181

4-(4-(3-butenyl)phenyl)-3′-fluoro-4′-chlorotolan

Compound No. 182

4-(4-(3-E-pentenyl)phenyl)-3′-fluoro-4′-chlorotolan

Compound No. 183

4-(4-(3-butenyl)phenyl)-4′-bromotolan

Compound No. 184

4-(4-(3-E-pentenyl)phenyl)-4′-bromotolan

Compound No. 185

4-(4-(3-butenyl)phenyl)-4′-trifluoromethyltolan

Compound No. 186

4-(4-(3-E-pentenyl)phenyl)-4′-trifluoromethyltolan

Compound No. 187

4-(4-(3-butenyl)phenyl)-4′-trifluoromethoxytolan

Compound No. 188

4-(4-(3-E-pentenyl)phenyl)-4′-trifauoromethoxytolan

Compound No. 189

4-(4-(3-butenyl)phenyl)-4′-(1-fluoro -2,2,2-trifluoroethyl)eoxytolan

Compound No. 190

4-(4-(3-E-pentenyl)phenyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 191

trans-1-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)ethynyl-4-ethylcyclohexane

Compound No. 192

trans-1-4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)ethynyl-4-ethyicyciohexane

Compound No. 193

trans-1-(4-(trans-4-(3-butenyl)cyclohexyl)-2,6-difluorophenyl)ethynyl-4-ethylcyciohexane

Compound No. 194

trans-1-4-(4-(trans-4-(3-E-pentenyl)cylohexyl)-2,6-difluorophenyl)ethynyl-4-ethylcyclohexane

Compound No. 195

trans-1-(4-(trans-4-(3-butenyl)cyciohexyl)phenyl)ethynyl-4-ethoxycyclohexane

Compound No. 196

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)ethynyl-4-ethoxycyclohexane

Compound No. 197

trans-1-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)ethynyl-4-cyanocyclohexane

Compound No. 198

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)ethynyl-4-cyanocyclohexane

Compound No. 199

trans-1-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)ethynyl-4-chlorocyclohexane

Compound No. 200

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)ethynyl-4-chlorocyclohexane

Compound No. 201

trans-1-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)ethynyl-4-bromocyclohexane

Compound No. 202

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)ethynyl-4-bromocyclohexane

Compound No. 203

trans-1-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)ethynyl-4-trifluoromethylcyclohexane

Compound No. 204

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)ethynyl-4-trifluoromethylcyclohexane

Compound No. 205

trans-1-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)ethynyl-4-trifluoromethoxycyclohexane

Compound No. 206

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)ethynyl-4-trifluoromethoxycyclohexane

Compound No. 207

trans-1-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxycyclohexane

Compound No. 208

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxycyclohexane

Compound No. 209

trans-1-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-ethylcyclohexane

Compound No. 210

trans-1-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-ethylcyclohexane

Compound No. 211

trans-1-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)-2,6-difluorophenyl)ethynyl-4-ethylcyclohexane

Compound No. 212

trans-1-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)-2,6-difluorophenyl)ethynyl-4-ethylcyclohexane

Compound No. 213

trans-1-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-ethoxycyclohexane

Compound No. 214

trans-1-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-ethoxycyclohexane

Compound No. 215

trans-1-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-cyanocyclohexane

Compound No. 216

trans-1-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-cyanocyclohexane

Compound No. 217

trans-1-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-chlorocyclohexane

Compound No. 218

trans-1-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-chlorocyclohexane

Compound No. 219

trans-1-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-trifluoromethylcyclohexane

Compound No. 220

trans-1-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-trifluoromethylcyclohexane

Compound No. 221

trans-1-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-trifluoromethoxycyclohexane

Compound No. 222

trans-1-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-trifluoromethoxycyclohexane

Compound No. 223

trans-1-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxycyclohexane

Compound No. 224

trans-1-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxycyclohexane

Compound No. 225

trans-1-(4-(trans-4-(3-butenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-ethylcyclohexane

Compound No. 226

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-ethylcyclohexane

Compound No. 227

trans-1-(4-(trans-4-(3-butenyl)cyclohexylcarbonyloxy)-2,6-difluorophenyl)ethynyl-4-ethylcyclohexane

Compound No. 228

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexylcarbonyloxy)-2,6-difluorophenyl)ethynyl-4-ethylcyclohexane

Compound No. 229

trans-1-(4-(trans-4-(3-butenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-ethoxycyclohexane

Compound No. 230

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-ethoxycyclohexane

Compound No. 231

trans-1-(4-(trans-4-(3-butenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-cyanocyclohexane

Compound No. 232

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-cyanocyclohexane

Compound No. 233

trans-1-(4-(trans-4-(3-butenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-chlorocyclohexane

Compound No. 234

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-chlorocyclohexane

Compound No. 235

trans-1-(4-(trans-4-(3-butenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-trifluoromethylcyclohexane

Compound No. 236

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-trifluoromethylcyclohexane

Compound No. 237

trans-1-(4-(trans-4-(3-butenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-trifluoromethoxycyclohexane

Compound No. 238

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-trifluoromethoxycyclohexane

Compound No. 239

trans-1-(4-(trans-4-(3-butenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxycyclohexane

Compound No. 240

trans-1-(4-(trans-4-(3-E-pentenyl)cyclohexylcarbonyloxy)phenyl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxycyclohexane

Compound No. 241

trans-1-(4-(4-(3-butenyl)phenyl)phenyl)ethynyl-4-ethylcyclohexane

Compound No. 242

trans-1-(4-(4-(3-E-pentenyl)phenyl)phenyl)ethynyl-4-ethylcyclohexane

Compound No. 243

trans-1-(4-(4-(2-propenyloxy)phenyl)phenyl)ethynyl-4-ethynylcyclohexane

Compound No. 244

trans-1-(4-(4-(3-butenyl)phenyl)-2,6-difluorophenyl)ethynyl-4-ethylcyclohexane

Compound No. 245

trans-1-(4-(4-(3-E-pentenyl)phenyl)-2,6-difluorophenyl)ethynyl-4-ethylcyclohexane

Compound No. 246

trans-1-(4-(4-(3-butenyl)phenyl)phenyl)ethynyl-4-ethoxycyclohexane

Compound No. 247

trans-1-(4-(4-(3-E-pentenyl)phenyl)phenyl)ethynyl-4-ethoxycyclohexane

Compound No. 248

trans-1-(4-(4-(3-butenyl)phenyl)phenyl)ethynyl-4-cyanocyclohexane

Compound No. 249

trans-1-(4-(4-(3-E-pentenyl)phenyl)phenyl)ethynyl-4-cyanocyclohexane

Compound No. 250

trans-1-(4-(4-(3-butenyl)phenyl)phenyl)ethynyl-4-chlorocyclohexane

Compound No. 251

trans-1-(4-(4-(3-E-pentenyl)phenyl)phenyl)ethynyl-4-chlorocyclohexane

Compound No. 252

trans-1-(4-(4-(3-butenyl)phenyl)phenyl)ethynyl-4-trifluoromethylcyclohexane

Compound No. 253

trans-1-(4-(4-(3-E-pentenyl)phenyl)phenyl)ethynyl-4-trifluoromethylcyclohexane

Compound No. 254

trans-1-(4-(4-(3-butenyl)phenyl)phenyl)ethynyl-4-trifluoromethoxycyclohexane

Compound No. 255

trans-1-(4-(4-(3-E-pentenyl)phenyl)phenyl)ethynyl-4-trifluoromethoxycyclohexane

Compound No. 256

trans-1-(4-(4-(3-butenyl)phenyl)phenyl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxycyclohexane

Compound No. 257

trans-1-(4-(4-(3-E-pentenyl)phenyl)phenyl)ethynyl-4-(1-fluoro-2,2,2-trifluoroethyl)oxycyclohexane

Compound No. 258

4-(3-butenyl)-4′-(trans-4-propylcyclohexyl)tolan

Compound No. 258-1

4-(3-butenyl)-4′-(trans-4-pentylcyclohexyl)tolan

C•63.1•S•112.6•N•190.9•I

Compound No. 259

trans-1-(4-(3-butenyl)phenyl)ethynyl-4-(4-ethylphenyl)cyclohexane

Compound No. 260

trans-1-(4-(3-E-pentenyl)phenyl)ethynyl-4-(4-ethylphenyl)cyclohexane

Compound No. 261

trans-1-(4-(3-butenyl)-2,6-difluorophenyl)ethynyl-4-(4-ethylphenyl)cyclohexane

Compound No. 262

trans-1-(4-(3-E-pentenyl)-2,6-difluorophenyl)ethynyl-4-(4-ethylphenyl)cyclohexane

Compound No. 263

trans-1-(4-(3-butenyl)phenyl)ethynyl-4-(4-ethoxyphenyl)cyclohexane

Compound No. 264

trans-1-(4-(3-E-pentenyl)phenyl)ethynyl-4-(4-ethoxyphenyl)cyclohexane

Compound No. 265

trans-1-(4-(3-butenyl)phenyl)ethynyl-4-(4-cyanophenyl)cyclohexane

Compound No. 266

trans-1-(4-(3-E-pentenyl)phenyl)ethynyl-4-(4-cyanophenyl)cyclohexane

Compound No. 267

trans-1-(4-(3-butenyl)phenyl)ethynyl-4-(4-chlorophenyl)cyclohexane

Compound No. 268

trans-1-(4-(3-E-pentenyl)phenyl)ethynyl-4-(4-chlorophenyl)cyclohexane

Compound No. 269

trans-1-(4-(3-butenyl)phenyl)ethynyl-4-(4-trifluoromethylphenyl)cyclohexane

Compound No. 270

trans-1-(4-(3-E-pentenyl)phenyl)ethynyl-4-(4-trifluoromethylphenyl)cyclohexane

Compound No. 271

trans-1-(4-(3-butenyl)phenyl)ethynyl-4-(4-trifluoromethoxyphenyl)cyclohexane

Compound No. 272

trans-1-(4-(3-E-pentenyl)phenyl)ethynyl-4-(4-trifluoromethoxyphenyl)cyclohexane

Compound No. 273

trans-1-(4-(3-butenyl)phenyl)ethynyl-4-(4-(1-fluoro-2,2,2-trifluoroethyl)oxyphenyl)cyclohexane

Compound No. 274

trans-1-(4-(3-E-pentenyl)phenyl)ethynyl-4-(4-(1-fluoro-2,2,2-trifluoroethyl)oxyphenyl)cyclohexane

Compound No. 275

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-4′-methyltolan

Compound No. 276

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-4′-methyltolan

Compound No. 277

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-4′-propyltolan

Compound No. 278

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-4′-propyltolan

Compound No. 279

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-4′-butyltolan

Compound No. 280

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl-4′-pentyltolan

Compound No. 281

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-2,6-difluoro-4′-methyltolan

Compound No. 282

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-2,6-difluoro-4′-methyltolan

Compound No. 283

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-2,6-difluoro-4′-propyltolan

Compound No. 284

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-2,6-difluoro-4′-propyltolan

Compound No. 285

4-(trans-4-(trans-4-(2-propenyloxymethyl)cyclohexyl)cyclohexyl)-4′-ethyltolan

Compound No. 286

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-4′-ethoxytolan

Compound No. 287

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-4′-ethoxytolan

Compound No. 288

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-4′-propoxytolan

Compound No. 289

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-4′-propoxytolan

Compound No. 290

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-4′-cyanotolan

Compound No. 291

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-4′-cyanotolan

Compound No. 292

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-3′-fluoro-4′-cyanotolan

Compound No. 293

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-3′-fluoro-4′-cyanotolan

Compound No. 294

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-4′-chlorotolan

Compound No. 295

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-4′-chlorotolan

Compound No. 296

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-3′-fluoro-4′-chlorotolan

Compound No. 297

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-3′-fluoro-4′-chlorotolan

Compound No. 298

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-4′-bromotolan

Compound No. 299

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-4′-bromotolan

Compound No. 300

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-4′-trifluoromethyltolan

Compound No. 301

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-4′-trifluoromethyltolan

Compound No. 302

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-4′-trifluoromethoxytolan

Compound No. 303

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-4′-trifluoromethoxytolan

Compound No. 304

4-(trans-4-(trans-4-(3-butenyl)cyclohexyl)cyclohexyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 305

4-(trans-4-(trans-4-(3-E-pentenyl)cyclohexyl)cyclohexyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 306

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-4′-methyltolan

Compound No. 307

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-4′-methyltolan

Compound No. 308

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-4′-propyltolan

Compound No. 309

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-4′-propyltolan

Compound No. 310

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-2,6-difluoro-4′-methyltolan

Compound No. 311

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-2,6-difluoro-4′-methyltolan

Compound No. 312

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-2,6-difluoro-4′-propyltolan

Compound No. 313

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-2,6-difluoro-4′-propyltolan

Compound No. 314

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-4′-ethoxytolan

Compound No. 315

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-4′-ethoxytolan

Compound No. 316

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-4′-propoxytolan

Compound No. 317

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-4′-propoxytolan

Compound No. 318

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-4′-cyanotolan

Compound No. 319

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-4′-cyanotolan

Compound No. 320

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-3′-fluoro-4′-cyanotolan

Compound No. 321

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-3′-fluoro-4′-cyanotolan

Compound No. 322

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-4′-chlorotolan

Compound No. 323

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-4′-chlorotolan

Compound No. 324

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-3′-fluoro-4′-chlorotolan

Compound No. 325

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-3′-fluoro-4′-chlorotolan

Compound No. 326

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-4′-bromotolan

Compound No. 327

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-4′-bromotolan

Compound No. 328

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-4′-trifluoromethyltolan

Compound No. 329

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-4′-trifluoromethyltolan

Compound No. 330

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-4′-trifluoromethoxytolan

Compound No. 331

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-4′-trifluoromethoxytolan

Compound No. 332

4-(trans-4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)cyclohexyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 333

4-(trans-4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)cyclohexyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 334

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-4′-methyltolan

Compound No. 335

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-4′-methyltolan

Compound No. 336

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-4′-propyltolan

Compound No. 337

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-4′-propyltolan

Compound No. 338

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-2,6-difluoro-4′-methyltolan

Compound No. 339

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-2,6-difluoro-4′-methyltolan

Compound No. 340

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-2,6-difluoro-4′-propyltolan

Compound No. 341

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-2,6-difluoro-4′-propyltolan

Compound No. 342

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-4′-ethoxytolan

Compound No. 343

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-4′-ethoxytolan

Compound No. 344

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-4′-propoxytolan

Compound No. 345

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-4′-propoxytolan

Compound No. 346

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-4′-cyanotolan

Compound No. 347

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-4′-cyanotolan

Compound No. 348

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-3′-fluoro-4′-cyanotolan

Compound No. 349

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-3′-fluoro-4′-cyanotolan

Compound No. 350

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-4′-chlorotolan

Compound No. 351

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-4′-chlorotolan

Compound No. 352

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-3′-fluoro-4′-chlorotolan

Compound No. 353

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-3′-fluoro-4′-chlorotolan

Compound No. 354

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-4′-bromotolan

Compound No. 355

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-4′-bromotolan

Compound No. 356

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-4′-trifluoromethyltolan

Compound No. 357

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-4′-trifluoromethyltolan

Compound No. 358

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-4′-trifluoromethoxytolan

Compound No. 359

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-4′-trifluoromethoxytolan

Compound No. 360

4-(4-(trans-4-(3-butenyl)cyclohexyl)phenyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 361

4-(4-(trans-4-(3-E-pentenyl)cyclohexyl)phenyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 362

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-4′-methyltolan

Compound No. 363

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-4′-methyltolan

Compound No. 364

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-4′-propyltolan

Compound No. 365

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-4′-propyltolan

Compound No. 366

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-2,6-difluoro-4′-methyltolan

Compound No. 367

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-2,6-difluoro-4′-methyltolan

Compound No. 368

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-2,6-difluoro-4′-propyltolan

Compound No. 369

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-2,6-difluoro-4′-propyltolan

Compound No. 370

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-4′-ethoxytolan

Compound No. 371

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-2,6-difluoro-4′-ethoxytolan

Compound No. 372

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-4′-propoxytolan

Compound No. 373

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-2,6-difluoro-4′-propoxytolan

Compound No. 374

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-4′-cyanotolan

Compound No. 375

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-4′-cyanotolan

Compound No. 376

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-3′-fluoro-4′-cyanotolan

Compound No. 377

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-3′-fluoro-4′-cyanotolan

Compound No. 378

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-4′-chlorotolan

Compound No. 379

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-4′-chlorotolan

Compound No. 380

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-3′-fluoro-4′-chlorotolan

Compound No. 381

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-3′-fluoro-4′-chlorotolan

Compound No. 382

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-4′-bromotolan

Compound No. 383

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-4′-bromotolan

Compound No. 384

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-4′-trifluoromethyltolan

Compound No. 385

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-4′-trifluoromethyltolan

Compound No. 386

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-4′-trifluoromethoxytolan

Compound No. 387

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-4′-trifluoromethoxytolan

Compound No. 388

4-(4-(2-(trans-4-(3-butenyl)cyclohexyl)ethyl)phenyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 389

4-(4-(2-(trans-4-(3-E-pentenyl)cyclohexyl)ethyl)phenyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 390

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-4′-methyltolan

Compound No. 391

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-4′-methyltolan

Compound No. 392

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-4′-propyltolan

Compound No. 393

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-4′-propyltolan

Compound No. 394

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-2,6-difluoro-4′-methyltolan

Compound No. 395

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-2,6-difluoro-4′-methyltolan

Compound No. 396

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-2,6-difluoro-4′-propyltolan

Compound No. 397

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-2,6-difluoro-4′-propyltolan

Compound No. 398

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-4′-ethoxytolan

Compound No. 399

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-4′-ethoxytolan

Compound No. 400

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-4′-propoxytolan

Compound No. 401

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-4′-propoxytolan

Compound No. 402

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-4-cyanotolan

Compound No. 403

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-4′-cyanotolan

Compound No. 404

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-3′-fluoro-4′-cyanotolan

Compound No. 405

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-3′-fluoro-4′-cyanotolan

Compound No. 406

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-4′-chlorotolan

Compound No. 407

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-4′-chlorotolan

Compound No. 408

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-3′-fluoro-4′-chlorotolan

Compound No. 409

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-3′-fluoro-4′-chlorotolan

Compound No. 410

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-4′-bromotolan

Compound No. 411

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-4′-bromotolan

Compound No. 412

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-4′-trifluoromethyltolan

Compound No. 413

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-4′-trifluoromethyltolan

Compound No. 414

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-4′-trifluoromethoxytolan

Compound No. 415

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-4′-trifluoromethoxytolan

Compound No. 416

4-(trans-4-(4-(3-butenyl)phenyl)cyclohexyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 417

4-(trans-4-(4-(3-E-pentenyl)phenyl)cyclohexyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 418

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-4′-methyltolan

Compound No. 419

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-4′-methyltolan

Compound No. 420

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-4′-propyltolan

Compound No. 421

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-4′-propyltolan

Compound No. 422

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-2,6-difluoro-4′-methyltolan

Compound No. 423

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-2,6-difluoro-4′-methyltolant

Compound No. 424

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-2,6-difluoro-4′-propyltolan

Compound No. 425

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-2,6-difluoro-4′-propyltolan

Compound No. 426

4-(4-(4-(3-butenyl)-2,6-difluorophenylethynyl)phenyl)-4′-methyltolan

Compound No. 427

4-(4-(4-(3-E-pentenyl)-2,6-difluorophenylethynyl)phenyl)-4′-methyltolan

Compound No. 428

4-(4-(4-(3-butenyl)-2,6-difluorophenylethynyl)phenyl)-4′-propyltolan

Compound No. 429

4-(4-(4-(3-E-pentenyl)-2,6-difluorophenylethynyl)phenyl)-4′-propyltolan

Compound No. 430

4-(4-(4-(3-butenyl)-2,6-difluorophenylethynyl)phenyl)-2,6-difluoro-4′-methyltolan

Compound No. 431

4-(4-(4-(3-E-pentenyl)-2,6-difluorophenylethynyl)phenyl)-2,6-difluoro-4′-methyltolan

Compound No. 432

4-(4-(4-(3-butenyl)-2,6-difluorophenylethynyl)phenyl)-2,6-difluoro-4′-propyltolan

Compound No. 433

4-(4-(4-(3-E-pentenyl)-2,6-difluorophenylethynyl)phenyl)-2,6-difluoro-4′-propyltolan

Compound No. 434

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-4′-ethoxytolan

Compound No. 435

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-4′-ethoxytolan

Compound No. 436

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-4′-propoxytolan

Compound No. 437

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-4′-propoxytolan

Compound No. 438

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-4′-cyanotolan

Compound No. 439

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-4′-cyanotolan

Compound No. 440

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-3′-fluoro-4′-cyanotolan

Compound No. 441

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-3′-fluoro-4′-cyanotolan

Compound No. 442

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-4′-chlorotolan

Compound No. 443

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-4′-chlorotolan

Compound No. 444

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-3′-fluoro-4′-chlorotolan

Compound No. 445

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-3′-fluoro-4′-chlorotolan

Compound No. 446

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-4′-bromotolan

Compound No. 447

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-4′-bromotolan

Compound No. 448

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-4′-trifluoromethyltolan

Compound No. 449

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-4′-trifluoromethyltolan

Compound No. 450

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-4′-trifluoromethoxytolan

Compound No. 451

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-4′-trifluoromethoxytolan

Compound No. 452

4-(4-(4-(3-butenyl)phenylethynyl)phenyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

Compound No. 453

4-(4-(4-(3-E-pentenyl)phenylethynyl)phenyl)-4′-(1-fluoro-2,2,2-trifluoroethyl)oxytolan

EXAMPLE 9 (Use Example 1)

Nematic liquid crystal of a liquid crystal composition comprising

4-(trans-4-propylcyclohexyl)benzonitrile 24% (% by weight, the same willbe applied in the followings)

4-(trans-4-pentylcyclohexyl)benzonitrile 36%

4-(trans-4-heptylcyclohexyl)benzonitrile 25%, and

4-(4-propylphenyl)benzonitrile 15%

had a clearing point (T_(NI)) of 71.7° C. When this liquid crystalcomposition was filled in a TN cell (twisted nematic cell) having athickness of 9 μm, its operation threshold voltage was 1.78 V, value ofdielectric anisotropy (Δ∈) was +11.0, value of optical anisotropy (Δn)was 0.137, and viscosity at 20° C. (η₂₀) was 27.2 mPa·s. Assuming thisliquid crystal composition as mother liquid crystal (hereinafterreferred to as Mother liquid crystal A), 15% of the4-(trans-4-(3-butenyl)cyclohexyl)-4′-ethyltolan (Compound No. 45)described in Example 1 was mixed with 85% of Mother liquid crystal A,and physical properties of the mixture were determined. As the result,it was found that T_(NI) was 88.3° C., V_(th) was 1.89 V, Δ∈ was 10.4,Δn was 0.155, and η₂₀ was 25.2 mPa·s. Whereas this liquid crystalcomposition was left in a freezer at −20° C. for 20 days, neitherprecipitation of crystals nor development of smectic phase was observed.

EXAMPLE 10 (Use Example 2)

To 85% of Mother liquid crystal composition A described in Example 9 wasmixed 15% of the4-(trans-4-(3-butenyl)cyclohexyl)-2,6-difluoro-4′-ethyltolan (CompoundNo. 56) described in Example 2, and physical properties of the mixturewere determined. As the result, it was found that T_(NI) was 83.0° C.,V_(th) was 1.86 V, Δ∈ was 10.3, Δn was 0.154, and η₂₀ was 26.1 mPa·s.

EXAMPLE 11 (Use Example 3)

To 85% of Mother liquid crystal composition A described in Example 9 wasmixed 15% of 4-(3-butenyl)-4′-pentyltolan (Compound No. 7), and physicalproperties of the mixture were determined. As the result, it was foundthat T_(NI) was 67.1° C., V_(th) was 1.72 V, Δ∈ was 10.2, Δn was 0.150,and η₂₀ was 21.6 mPa·s.

EXAMPLE 12 (Use Example 4)

To 85% of Mother liquid crystal composition A described in Example 9 wasmixed 15% of 4-(3-butenyl)-4′-heptoxytolan (Compound No. 12-1), andphysical properties of the mixture were determined. As the result, itwas found that T_(NI) was 66.7° C., V_(th) was 1.59 V, Δ∈ was 9.8, Δnwas 0.144, and η₂₀ was 25.4 mPa·s.

EXAMPLE 13 (Use Example 5)

To 85% of Mother liquid crystal composition A described in Example 9 wasmixed 15% of 4-(3-butenyl)-4′-(trans-4-pentylcyclohexyl)tolan (CompoundNo. 258-1), and physical properties of the mixture were determined. Asthe result, it was found that T_(NI) was 87.5° C., V_(th) was 1.82 V, Δ∈was 10.3, Δn was 0.153, and η₂₀ was 25.9 mPa·s.

Whereas the liquid crystal compositions of these Examples 10 to 13 wereleft in a freezer at −20° C. for 20 days, respectively, neitherprecipitation of crystals nor development of smectic phase was observed.

In the same manner, the following liquid crystal compositions wereprepared and their physical properties were determined. (In thefollowings, the meaning of abbreviation is the same as described above.Also, in the following, η₂₀ is abbreviated as η.)

EXAMPLE 14 (Use Example 6)

V2-BTB-5 5.0% V2-BTB-O7 5.0% 1V2-BEB(F,F)—C 5.0% 3-HB-C 25.0% 1-BTB-35.0% 3-HH-4 11.0% 3-HHB-1 11.0% 3-HHB-3 9.0% 3-H2BTB-2 4.0% 3-H2BTB-34.0% 3-H2BTB-4 4.0% 3-HB(F)TB-2 6.0% 3-HB(F)TB-3 6.0%

T_(NI)=93.5 (° C.)

η=16.6 (mPa·s)

Δn=0.159

Δ∈=7.2

V_(th)=2.02 (V)

EXAMPLE 15 (Use Example 7)

V2-BTBH-5 4.0% 2O1-BEB(F)—C 5.0% 3O1-BEB(F)—C 15.0% 4O1-BEB(F)—C 13.0%5O1-BEB(F)—C 13.0% 2-HHB(F)—C 15.0% 3-HHB(F)—C 15.0% 3-HB(F)TB-2 4.0%3-HB(F)TB-3 4.0% 3-HB(F)TB-4 4.0% 3-HHB-1 4.0% 3-HHB-O1 4.0%

T_(NI)=92.1 (° C.)

η=86.1 (mPa·s)

Δn=0.155

Δ∈=31.1

V_(th)=0.86 (V)

EXAMPLE 16 (Use Example 8)

V2-BTB-5 4.0% V2-BTB-O7 5.0% V2-BTBH-5 4.0% 5-PyB-F 4.0% 3-PyB(F)—F 4.0%2-BB-C 5.0% 2-PyB-2 2.0% 3-PyB-2 2.0% 4-PyB-2 2.0% 6-PyB-O5 3.0%6-PyB-O6 3.0% 6-PyB-O7 3.0% 6-PyB-O8 3.0% 3-PyBB-F 6.0% 4-PyBB-F 6.0%5-PyBB-F 6.0% 3-HHB-1 6.0% 3-HHB-3 4.0% 2-H2BTB-2 4.0% 2-H2BTB-3 4.0%2-H2BTB-4 5.0% 3-H2BTB-2 5.0% 3-H2BTB-3 5.0% 3-H2BTB-4 5.0%

T_(NI)=96.5 (° C.)

η=33.7 (mPa·s)

Δn=0.208

Δ∈=5.9

V_(th)=2.68 (V)

EXAMPLE 17 (Use Example 9)

V2-BTB-5 5.0% V2-HBTB-2 3.0% 3-GB-C 10.0% 4-GB-C 10.0% 2-BEB-C 12.0%3-BEB-C 4.0% 3-PyB(F)—F 6.0% 3-HEB-O4 8.0% 4-HEB-O2 6.0% 5-HEB-O1 6.0%3-HEB-O2 5.0% 5-HEB-O2 4.0% 5-HEB-5 5.0% 1O-BEB-2 4.0% 3-HHB-1 3.0%3-HHEBB-C 3.0% 3-HBEBB-C 3.0% 5-HBEBB-C 3.0%

T_(NI)=70.6 (° C.)

η=38.4 (mPa·s)

Δn=0.135

Δ∈=11.8

V_(th)=1.19 (V)

EXAMPLE 18 (Use Example 10)

V2-BTB-O7 3.0% V2-HB(F,F)TB-2 4.0% 3-HB-C 18.0% 1O1-HB-C 10.0% 3-HB(F)—C10.0% 2-PyB-2 2.0% 3-PyB-2 2.0% 4-PyB-2 2.0% 1O1-HH-3 7.0% 2-BTB-O1 7.0%3-HHB-1 7.0% 3-HHB-F 4.0% 3-HHB-O1 4.0% 3-HHB-3 4.0% 3-H2BTB-2 3.0%3-H2BTB-3 3.0% 2-PyBH-3 4.0% 3-PyBH-3 3.0% 3-PyBB-2 3.0%

T_(NI)=78.7 (° C.)

η=18.1 (mPa·s)

Δn=0.148

Δ∈=8.1

V_(th)=1.75 (V)

EXAMPLE 19 (Use Example 11)

V2-HBTB-2 4.0% V2-HB(F,F)TB-2 4.0% 2O1-BEB(F)—C 5.0% 3O1-BEB(F)—C 12.0%5O1-BEB(F)—C 4.0% 1V2-BEB(F,F)—C 10.0% 3-HH-EMe 10.0% 3-HB-O2 18.0%7-HEB-F 2.0% 3-HHEB-F 2.0% 5-HHEB-F 2.0% 3-HBEB-F 4.0% 2O1-HBEB(F)—C2.0% 3-HB(F)EB(F)—C 2.0% 3-HBEB(F,F)—C 2.0% 3-HHB-F 4.0% 3-HHB-O1 4.0%3-HHB-3 5.0% 3-HEBEB-F 2.0% 3-HEBEB-1 2.0%

T_(NI)=78.1 (° C.)

η=35.7 (mPa·s)

Δn=0.127

Δ∈=24.0

V_(th)=0.82 (V)

EXAMPLE 20 (Use Example 12)

V2-BTB-5 5.0% V2-HBTB-2 7.0% 2-HHB(F)—F 17.0% 3-HHB(F)—F 17.0%5-HHB(F)—F 16.0% 2-H2HB(F)—F 10.0% 5-H2HB(F)—F 10.0% 2-HBB(F)—F 6.0%3-HBB(F)—F 6.0% 5-HBB(F)—F 6.0%

T_(NI)=103.9 (° C.)

η=22.6 (mPa·s)

Δn=0.112

Δ∈=5.0

=V_(th)=2.27 (V)

EXAMPLE 21 (Use Example)

V2-HB(F,F)TB-2 7.0% V2-BTB-O7 3.0% 7-HB(F,F)—F 3.0% 3-HB-O2 7.0%2-HHB(F)—F 10.0% 3-HHB(F)—F 10.0% 5-HHB(F)—F 10.0% 2-HBB(F)—F 9.0%3-HBB(F)—F 9.0% 5-HBB(F)—F 9.0% 2-HBB-F 4.0% 3-HBB-F 4.0% 3-HBB(F,F)—F5.0% 5-HBB(F,F)—F 10.0%

T_(NI)=86.5 (° C.)

η=24.6 (mPa·s)

Δn=0.124

Δ∈=5.6

V_(th)=2.14 (V)

EXAMPLE 22 (Use Examle 14)

V2-BTB-5 4.0% V2-BTB-O7 4.0% 3-HB-CL 10.0% 1O1-HH-5 5.0% 2-HBB(F)—F 8.0%3-HBB(F)—F 8.0% 5-HBB(F)—F 14.0% 4-HHB-CL 8.0% 5-HHB-CL 8.0%3-H2HB(F)—CL 4.0% 3-HBB(F,F)—F 10.0% 5-H2BB (F,F)—F 9.0% 3-HB(F)VB-24.0% 3-HB(F)VB-3 4.0%

T_(NI)=94.1 (° C.)

η=21.6 (mPa·s)

Δn=0.140

Δ∈=4.8

V_(th)=2.41 (V)

EXAMPLE 23 (Use Example 15)

V2-BTB-5 7.0% V2-BTB-O7 7.0% V2-BTBH-5 7.0% 3-HHB(F,F)—F 9.0%3-H2HB(F,F)—F 8.0% 4-H2HB(F,F)—F 8.0% 5-H2HB(F,F)—F 8.0% 5-HBB(F,F)—F20.0% 3-H2BB(F,F)—F 10.0% 5-HHBB(F,F)—F 3.0% 5-HHEBB-F 2.0%3-HH2BB(F,F)—F 3.0% 1O1-HBBH-4 4.0% 1O1-HBBH-5 4.0%

T_(NI)=105.5 (° C.)

η=29.9 (mPa·s)

Δn=0.137

Δ∈=7.6

V_(th)=2.46 (V)

EXAMPLE 24 (Use Example 16)

V2-BTB-O7 5.0% V2-BTBH-5 5.0% 5-HB-F 12.0% 6-HB-F 9.0% 7-HB-F 7.0%2-HHB-OCF3 7.0% 3-HHB-OCF3 7.0% 4-HHB-OCF3 7.0% 5-HHB-OCF3 5.0%3-HH2B-OCF3 4.0% 5-HH2B-OCF3 4.0% 3-HHB(F,F)—OCF3 5.0% 3-HBB(F)—F 10.0%3-HH2B(F)—F 3.0% 3-HB(F)BH-3 3.0% 5-HBBH-3 3.0% 3-HHB(F,F)—OCF2H 4.0%

T_(NI)=87.0 (° C.)

η=14.1 (mPa·s)

Δn=0.100

Δ∈=4.1

V_(th)=2.78 (V)

EXAMPLE 25 (Use Example 17)

V2-HBTB-2 5.0% V2-HB(F,F)TB-2 5.0% 2-HHB(F)—F 2.0% 3-HHB(F)—F 2.0%5-HHB(F)—F 2.0% 2-HBB(F)—F 6.0% 3-HBB(F)—F 6.0% 2-H2BB(F)—F 9.0%3-H2BB(F)—F 9.0% 3-HBB(F,F)—F 25.0% 5-HBB(F,F)—F 19.0% 1O1-HBBH-4 5.0%1O1-HBBH-5 5.0%

T_(NI)=103.4 (° C.)

η=34.4 (mPa·s)

Δn=0.147

Δ∈=7.1

V_(th)=2.09 (V)

EXAMPLE 26 (Use Example 18)

V2-BTB-5 5.0% V2-HBTB-2 5.0% V2-HB(F,F)TB-2 5.0% 3-H2HB(F,F)—F 7.0%5-H2HB(F,F)—F 8.0% 3-HHB(F,F)—F 10.0% 4-HHB(F,F)—F 5.0% 3-HH2B(F,F)—F9.0% 5-HH2B(F,F)—F 9.0% 5-HHB(F,F)—F 15.0% 3-HBEB(F,F)—F 2.0%4-HBEB(F,F)—F 2.0% 5-HBEB(F,F)—F 2.0% 3-HHEB(F,F)—F 10.0% 4-HHEB(F,F)—F3.0% 5-HHEB(F,F)—F 3.0%

T_(NI)=92.5 (° C.)

η=28.2 (mPa·s)

Δn=0.111

Δ∈=10.5

V_(th)=2.21 (V)

COMPARATIVE EXAMPLE 1

As a compound to be compared to the compounds of the present invention,the compound (23) described in Mol. Cryst. Liq. Cryst., vol. 141, p 279(1986) was actually synthesized, and assumed to be comparative compound.

Liquid crystal composition in which 85% of Mother liquid crystal Adescribed above and 15% of the comparative compound (23) were mixed wasprepared, and its optical anisotropy (Δn; extrapolation value) wasdetermined. Its result, and phase transition temperatures andmiscibility of the compound are shown in Table 2 together with theresults of Examples 9 and 10.

TABLE 2 Phase transition temperature (° C.) Δn^(a)) Miscibility^(b))

C.102.N.197.I 0.249 7

C.58.9.S.115.1.N.175.I 0.257 >20

C.75.1.N.174.6.I 0.250 >20 ^(a))Extrapolatied value ^(b))Number of dayspassed by the time when precipitation of crystals or appearance ofsmectic phase was confirmed after initiation of leaving of the compoundin a freezer at −20° C.

As shown in Table 2, whereas the comparative compound (23) had atransition temperature from crystal to liquid crystal phase of 102° C.,compounds (24) and (25) had a phase transition temperature of 58.9° C.and 75.1° C., respectively. With respect to the temperature range ofliquid crystal phase, whereas the range of the compound (23) was 95° C.,that of compounds (24) and (25) were 116° C. and 100° C., respectively.As will be seen from these results, the compounds of the presentinvention are remarkably low in the lower temperature limit forexhibiting liquid crystal phase and wide in the temperature rangecompared with conventional liquid crystalline compounds. Accordingly,liquid crystal compositions comprising the compound of the presentinvention can be considered to have wide range of liquid crystal displayin practical use. As shown in Table 2, the value of optical anisotropyof the compounds of the present invention were also higher than that ofconventional liquid crystalline compounds. Accordingly, it is possibleto reduce the thickness of liquid crystal cells and increase theresponse speed in cells by using liquid crystal compositions comprisingthe compound of the present invention. Besides, whereas solidsexhibiting smectic phase were precipitated in 7 days when the compound(23) was left in a freezer at −20° C., precipitation of crystals or thelikes was not caused in 20 days or more with respect to the compounds(24) and (25) of the present invention to confirm that the compounds ofthe present invention have remarkably excellent miscibility at lowtemperatures. As described above, the compounds of the present inventionhave characteristics which can not be found in known liquid crystalcompounds, and have excellent properties as liquid crystal material.

INDUSTRIAL APPLICABILITY

As described above, according to the present invention, (a) tolanderivatives, novel liquid crystalline compounds having sufficiently highoptical anisotropy, high dielectric anisotropy, large ratio of elasticconstants, excellent miscibility with other liquid crystallinecompounds, low viscosity, and chemical and physical stability; (b)liquid crystal compositions comprising the tolan derivative; and (c)liquid crystal display devices including the liquid crystal compositioncan be provided.

What is claimed is:
 1. A liquid crystalline alkenyltolan derivativeexpressed by the general formula (1)C_(t)H_(2t−1)—G—(CH₂)_(m)—A₁—B₁—(A₂—B₂)_(n)—(A₃—B₃)_(p)—A₄—X  (1)wherein A₁, A₂, A₃, and A₄ independently represent a 1,4-cyclohexylene,1,4-phenylene in which one or two hydrogen atoms may be replaced by afluorine atom(s), dioxane-2,5-diyl, or pyrimidine-2,5-diyl group; B₁,B₂, and B₃ independently represent a covalent bond, an 1,2-ethylene,1,2-ethenylene, 1,2-ethynylene, oxymethylene, methylenoxy or carbonyloxyprovided that at least one of B₁, B₂, and B₃ represents an1,2-ethynylene group; G represents a covalent bond or an oxygen atom;C_(t)H_(2t−1) represents an alkenyl group having t carbon atoms whereint is an integer of 2 to 10; m is an integer of 0 to 2; n and p areindependently an integer of 0 or 1; X represents an alkyl group having 1to 10 carbon atoms, a fluoroalkyl group having 1 to 10 carbon atoms, achlorine atom, a bromine atom, or a cyano group wherein one or moremethylene groups or fluoromethylene groups in the alkyl group or thefluoroalkyl group may be replaced by an oxygen atom(s) or an1,2-ethenylene group, but adjacent two methylene groups should not besimultaneously replaced by them; provided that when A₄ represents1,4-phenylene group which is not substituted with a fluorine atom(s),there is no case that G represents a covalent bond and t+m=3simultaneously; provided that when A₁ represents 1,4-phenylene groupwhich is not substituted with a fluorine atom(s), B₁ represents1,2-ethynylene, and G represents a covalent bond, there is no case thatt+m=3; provided that when A₁ represents a 1,4-phenylene group whereinfluorine atoms replace two hydrogens and A₄ represents a1,4-cyclohexane, B₁ is not a triple covalent bond; and each element inthe molecule may be its isotope.
 2. The liquid crystalline alkenyltolanderivative according to claim 1 wherein n and p are
 0. 3. The liquidcrystalline alkenyltolan derivative according to claim 1 wherein n is 1and p is
 0. 4. The liquid crystalline alkenyltolan derivative accordingto claim 1 wherein n and p are
 1. 5. The liquid crystalline alkenyltolanderivative according to claim 2 wherein X represents a chlorine atom, abromine atom, a cyano group, or a fluoroalkyl group having 1 to 10carbon atoms in which one or more fluoromethylene groups may be replacedby an oxygen atom(s) or an 1,2-ethenylene group(s).
 6. The liquidcrystalline alkenyltolan derivative according to claim 2 wherein Xrepresents an alkyl group having 1 to 10 carbon atoms in which one ormore methylene groups may be replaced by an oxygen atom(s) or an1,2-ethenylene group(s); and A₁ and A₄ independently represent a1,4-phenylene group in which one or two hydrogen atoms may be replacedby a fluorine atom(s).
 7. The liquid crystalline alkenyltolan derivativeaccording to claim 2 wherein G represents a covalent bond, t+m=4, and adouble bond exists at a terminal of the molecule.
 8. The liquidcrystalline alkenyltolan derivative according to claim 2 wherein Grepresents a covalent bond, t+m=5, and a double bond exists at a secondposition counting from a terminal of the molecule.
 9. The liquidcrystalline alkenyltolan derivative according to claim 3 wherein Xrepresents a chlorine atom, a bromine atom, a cyano group, or afluoroalkyl group having 1 to 10 carbon atoms in which one or morefluoromethylene groups may be replaced by an oxygen atom(s) or an1,2-ethenylene group(s).
 10. The liquid crystalline alkenyltolanderivative according to claim 3 wherein X represents an alkyl grouphaving 1 to 10 carbon atoms in which one or more methylene groups may bereplaced by an oxygen atom(s) or an 1,2-ethenylene group(s).
 11. Theliquid crystalline alkenyltolan derivative according to claim 10 whereinG represents a covalent bond, t+m=4, and a double bond exists at aterminal of the molecule.
 12. The liquid crystalline alkenyltolanderivative according to claim 10 wherein G represents a covalent bond,t+m=5, and a double bond exists at a second position counting from aterminal of the molecule.
 13. The liquid crystalline alkenyltolanderivative according to claim 11 wherein B₁ represents a covalent bondand B₂ represents an 1,2-ethynylene group.
 14. The liquid crystallinealkenyltolan derivative according to claim 12 wherein B₁ represents acovalent bond and B₂ represents an 1,2-ethynylene group.
 15. The liquidcrystalline alkenyltolan derivative according to claim 13 wherein A₁represents an 1,4-cyclohexylene group, and A₂ and/or A₄ represents an1,4-phenylene group in which a hydrogen atom(s) may be replaced by afluorine atom(s).
 16. The liquid crystalline alkenyltolan derivativeaccording to claim 15 wherein A₂ and A₄ represent 1,4-phenylene group inwhich a hydrogen atom(s) is not replaced by a fluorine atom(s).
 17. Theliquid crystalline alkenyltolan derivative according to claim 15 whereinA₂ represents 1,4-phenylene group in which two hydrogen atoms arereplaced by fluorine atoms and A₄ represents 1,4-phenylene group inwhich a hydrogen atom(s) is not replaced by a fluorine atom(s).
 18. Theliquid crystalline alkenyltolan derivative according to claim 3 whereinG represents a covalent bond, t+m=4, and a double bond exists at aterminal of the molecule.
 19. The liquid crystalline alkenyltolanderivative according to claim 3 wherein G represents a covalent bond,t+m=5, and a double bond exists at a second position counting from aterminal of the molecule.
 20. The liquid crystalline alkenyltolanderivative according to claim 4 wherein X represents a chlorine atom, abromine atom, a cyano group, or a fluoroalkyl group having 1 to 10carbon atoms in which one or more fluoromethylene groups may be replacedby an oxygen atom(s) or an 1,2-ethenylene group(s).
 21. The liquidcrystalline alkenyltolan derivative according to claim 4 wherein Xrepresents an alkyl group having 1 to 10 carbon atoms in which one ormore methylene groups may be replaced by an oxygen atom(s) or an1,2-ethenylene group(s).
 22. The liquid crystalline alkenyltolanderivative according to claim 21 wherein A₂ and/or A₄ represents1,4-phenylene group in which one or two hydrogen atoms may be replacedby an fluorine atom(s) and B₃ represents 1,2-ehtynylene group.
 23. Theliquid crystalline alkenyltolan derivative according to claim 21 whereinA₂ and/or A₃ represents an 1,4-phenylene group in which one or twohydrogen atoms may be replaced by an fluorine atom(s) and B₂ representsan 1,2-ehtynylene group.
 24. The liquid crystalline alkenyltolanderivative according to claim 23 wherein one or two hydrogen atoms of A₂and/or A₃ are replaced by an fluorine atom(s).
 25. The liquidcrystalline alkenyltolan derivative according to claim 4 wherein Grepresents a covalent bond, t+m=4, and a double bond exists at aterminal of the molecule.
 26. The liquid crystalline alkenyltolanderivative according to claim 4 wherein G represents a covalent bond,t+m=5, and a double bond exists at a second position counting from aterminal of the molecule.
 27. A liquid crystal composition comprising atleast two components and comprising at least one liquid crystallinecompound defined in claim
 1. 28. A liquid crystal compositioncomprising, as a first component, at least one liquid crystallinecompound defined in claim 1, and comprising, as a second component, atleast one compound selected from the group consisting of the compoundsexpressed by any one of the general formulas (2), (3), and (4)

wherein R₁ represents an alkyl group or alkyloxy group having 1 to 10carbon atoms; Y represents a fluorine atom or a chlorine atom; Q₁ and Q₂independently represent a hydrogen atom or a fluorine atom; r is 1 or 2;and Z₁ and Z₂ independently represent a covalent bond or —CH₂CH₂—.
 29. Aliquid crystal composition comprising, as a first component, at leastone compound defined in claim 1, and comprising, as a second component,at least one compound selected from the group consisting of thecompounds expressed by any one of the general formulas (5), (6), (7),(8), and (9)

wherein R₂ represents an alkyl group having 1 to 10 carbon atoms or analkenyl group having 2 to 10 carbon atoms, and any methylene group(—CH₂—) in the alkyl or the alkenyl group may be replaced by an oxygenatom (—O—), but adjacent two or more methylene groups are not replacedby an oxygen atom(s) simultaneously; Z₃ represents a covalent bond,—CH₂CH₂—, or —COO—; Q₃ and Q₄ independently represent a hydrogen atom ora fluorine atom; (E) represents an 1,4-cyclohexylene, 1,4-phenylene, ordioxane-2,5-diyl group; s is 0 or 1; R₃ represents an alkyl group having1 to 10 carbon atoms; Q₅ represents a hydrogen atom or a fluorine atom;k is 0 or 1; R₄ represents an alkyl group having 1 to 10 carbon atoms;(G₁) represents an 1,4-cyclohexylene or 1,4-phenylene group; Q₆ and Q₇independently represent a hydrogen atom or a fluorine atom; Z₄represents a covalent bond or —COO—; h is 0 or 1; R₅ and R₆independently represent an alkyl group, alkyloxy group, oralkyloxymethyl group, each having 1 to 10 carbon atoms; (H) representsan 1,4-cyclohexylene, pyrimidine-2,5-diyl, or 1,4-phenylene group; (J)represents an 1,4-cyclohexylene or 1,4-phenylene group; Z₅ represents acovalent bond, —CH₂CH₂—, —C≡C—, or —COO—; R₇ represents an alkyl groupor alkyloxy group, each having 1 to 10 carbon atoms; R₈ represents analkyl group, alkyloxy group, or alkyloxymethyl group, each having 1 to10 carbon atoms; (K) represents an 1,4-cyclohexylene orpyrimidine-2,5-diyl group; (L) and (M) independently represent an1,4-cyclohexylene or 1,4-phenylene group; Z₆ represents a covalent bond,—CH₂CH₂—, or —COO—; Z₇ represents a covalent bond, —C≡C—, or —COO—; andQ₈ represents a hydrogen atom or a fluorine atom.
 30. A liquid crystaldisplay device including a liquid crystal composition comprising atleast 2 components and comprising at least one liquid crystallinecompound defined in claim
 1. 31. A liquid crystal display deviceincluding a liquid crystal composition defined in claim
 28. 32. A liquidcrystal display device including a liquid crystal composition defined inclaim 29.